5909-59-1

Basic information

• Product Name: 10-(3-chloropropyl)-10H-phenothiazine
• Synonyms: 10-(3-chloropropyl)-10H-phenothiazine
• CAS NO: 5909-59-1
• Molecular Formula: C₁₅H₁₄ClNS
• Molecular Weight: 276
• Mol File: 5909-59-1.mol
• Article Data: 28

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 10-(3-chloropropyl)-10H-phenothiazine(CAS DataBase Reference)
• NIST Chemistry Reference: 10-(3-chloropropyl)-10H-phenothiazine(5909-59-1)
• EPA Substance Registry System: 10-(3-chloropropyl)-10H-phenothiazine(5909-59-1)

Safety Data

• Hazardous Substances Data: 5909-59-1(Hazardous Substances Data)

Usage

Uses

N-(3-Chloropropyl)phenothiazine is a useful reagent in synthesis of phenothiazine derivatives. It is an intermediate in the synthesis of Promazine Dimer Hydrochloride (P756305), which is an impurity of Promazine(P756300). Promazine is an antipsychotic and a tranquilizer.

Synthetic route

10H-phenothiazine (92-84-2) + 1,3-chlorobromopropane (109-70-6) → 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 4h;	90%
With sodium hydride In N,N-dimethyl-formamide	83.3%
Stage #1: 10H-phenothiazine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.333333h; Inert atmosphere; Stage #2: 1.3-chlorobromopropane In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;	82%

3-chloro-1-(10H-phenothiazin-10-yl)propan-1-one (4091-91-2) → 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1)

Conditions	Yield
Stage #1: 3-chloro-1-(10H-phenothiazin-10-yl)propan-1-one With diborane In tetrahydrofuran at 20℃; for 72h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=8;	88%

10H-phenothiazine (92-84-2) + 1,3-chlorobromopropane (109-70-6) → 10-allylphenothiazine (20962-92-9) + 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In various solvent(s) for 24h; Ambient temperature;	A 22% B 74%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In various solvent(s) for 24h; Product distribution; Ambient temperature; other solvent;	A 22% B 74%

3-(10H-phenothiazin-10-yl)propan-1-ol (63397-92-2) → 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + [β-(10-Phenothiazyl)propoxy]phosphonic acid dichloride (334990-68-0)

Conditions	Yield
With pyridine; trichlorophosphate In chloroform at -15 - 20℃; for 4h;	A n/a B 65.2%

10H-phenothiazine (92-84-2) + 1-iodo-3-chloro-propane (6940-76-7) → 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 9h;	37%
Stage #1: 10H-phenothiazine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Stage #2: 1-iodo-3-chloro-propane In N,N-dimethyl-formamide; mineral oil at 20℃;	8.3 g
Stage #1: 10H-phenothiazine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 1-iodo-3-chloro-propane In N,N-dimethyl-formamide at 0℃; for 1h;

3-chloropropyl p-toluenesulfonate (632-02-0) + n-butyllithium (109-72-8, 29786-93-4) + 10H-phenothiazine (92-84-2) → 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1)

10-(3-piperidin-1-yl-propyl)-10H-phenothiazine (3733-38-8) → 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1)

Conditions	Yield
With methanol; carbonochloridic acid 1-chloro-ethyl ester 1) 1,2-dichloroethane; Yield given. Multistep reaction;

phenothiazine nitranion (76069-04-0) + 1,3-chlorobromopropane (109-70-6) → 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1)

Conditions	Yield
In dimethyl sulfoxide

[β-(10-Phenothiazyl)propoxy]phosphonic acid dichloride (334990-68-0) → 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + [β-(10-Phenothiazyl)propoxy]phosphonic acid

Conditions	Yield
With water at 20℃; for 12h; Hydrolysis; Substitution;

10H-phenothiazine (92-84-2) → 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1)

Conditions	Yield
Multi-step reaction with 6 steps 1: 49.6 percent / aq. Triton B / 1 h / Heating 2: 52.56 percent / nAoh / methanol / 15 h / Heating 3: 63.9 percent / conc. H2SO4 / toluene / 12 h / Heating 4: 54.7 percent / LiAlH4 / diethyl ether / 20 °C 5: 65.2 percent / POCl3; pyridine / CHCl3 / 3.5 h / -15 - 20 °C 6: H2O / 12 h / 20 °C View Scheme

10H-phenothiazine-10-propanenitrile (1698-80-2) → 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 52.56 percent / nAoh / methanol / 15 h / Heating 2: 63.9 percent / conc. H2SO4 / toluene / 12 h / Heating 3: 54.7 percent / LiAlH4 / diethyl ether / 20 °C 4: 65.2 percent / POCl3; pyridine / CHCl3 / 3.5 h / -15 - 20 °C 5: H2O / 12 h / 20 °C View Scheme

3-(10H-phenothiazin-10-yl)propanoic acid (362-03-8) → 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 63.9 percent / conc. H2SO4 / toluene / 12 h / Heating 2: 54.7 percent / LiAlH4 / diethyl ether / 20 °C 3: 65.2 percent / POCl3; pyridine / CHCl3 / 3.5 h / -15 - 20 °C 4: H2O / 12 h / 20 °C View Scheme

β-(10-Phenothiazyl)propionic acid ethyl ester (107943-89-5) → 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 54.7 percent / LiAlH4 / diethyl ether / 20 °C 2: 65.2 percent / POCl3; pyridine / CHCl3 / 3.5 h / -15 - 20 °C 3: H2O / 12 h / 20 °C View Scheme

3-(10H-phenothiazin-10-yl)propan-1-ol (63397-92-2) → 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65.2 percent / POCl3; pyridine / CHCl3 / 3.5 h / -15 - 20 °C 2: H2O / 12 h / 20 °C View Scheme

1-methyl-piperazine (109-01-3) + 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) → Perazin (84-97-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; sodium iodide In N,N-dimethyl-formamide at 150℃; for 3h; Inert atmosphere;	99%

10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + potassium pyrrolide (16199-06-7) → 10-(3-Pyrrol-1-yl-propyl)-10H-phenothiazine (109850-28-4)

Conditions	Yield
In tetrahydrofuran	95%

10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) → 10-(3-azidopropyl)-10H-phenothiazine

Conditions	Yield
With sodium azide; tetrabutylammomium bromide In chloroform; water at 20℃; for 24h;	80%

10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + triphenylphosphine (603-35-0) → 3-(10H-phenothiazin-10-yl)propyl triphenylphosphonium chloride

Conditions	Yield
With sodium iodide In acetonitrile at 80℃; for 24h;	76%

10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + 3-piperazin-1-yl-propionitrile (34064-86-3) → 3-[4-(3-phenothiazin-10-ylpropyl)piperazin-1-yl]propionitrile (97115-68-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; sodium iodide In N,N-dimethyl-formamide for 2h; Heating;	75%

4-piperazin-1-yl-butyronitrile (5623-94-9) + 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) → 4-[4-(3-phenothiazin-10-ylpropyl)piperazin-1-yl]butyronitrile (916140-57-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; sodium iodide In N,N-dimethyl-formamide for 18h; Heating;	72%

piperazine (110-85-0) + 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) → N-Desmethylperazine (3240-48-0)

Conditions	Yield
With triethylamine; potassium iodide In N,N-dimethyl-formamide at 80℃; for 2h;	71%

10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + 2,2'-iminobis[ethanol] (111-42-2) → 2,2'-(3-phenothiazin-10-yl-propylazanediyl)-bis-ethanol (61852-29-7)

Conditions	Yield
With triethylamine; potassium iodide In N,N-dimethyl-formamide at 80℃; for 2h;	69%

10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + propan-1-ol-3-amine (156-87-6) → 3-((3-(10H-phenothiazin-10-yl)propyl)amino)propan-1-ol

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 10h;	65%

4-phenyl-1-piperazine (92-54-6) + 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) → 10-(3-(4-phenylpiperazin-1-yl)propyl)-10H-phenothiazine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; sodium iodide In N,N-dimethyl-formamide at 150℃; for 3h; Inert atmosphere;	62%

4-piperidone ethylene glycol ketal (40256-14-2) + 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) → 10-[3-(4-β-hydroxyethoxypiperidino)-propyl]-phenothiazine hydrochloride

Conditions	Yield
With hydrogenchloride; sodium iodide; triethylamine In butanone	55%

10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + 2‐(piperazin‐1‐yl)acetonitrile (58619-56-0) → [4-(3-phenothiazin-10-ylpropyl)piperazin-1-yl]acetonitrile (102447-20-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; sodium iodide In N,N-dimethyl-formamide for 18h; Heating;	54%

10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + benzoic acid hydrazide (613-94-5) → N'-(3-(10H-phenothiazin-10-yl)propyl)benzohydrazide

Conditions	Yield
With triethylamine In isopropyl alcohol at 90℃; for 12h;	20%

isoniazid (54-85-3) + 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) → N'-(3-(10H-phenothiazin-10-yl)propyl)isonicotinohydrazide

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 25℃;	18%

piperidine (110-89-4) + 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) → 10-(3-piperidin-1-yl-propyl)-10H-phenothiazine (3733-38-8)

Conditions	Yield
With copper

methylthiol (74-93-1) + 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) → 10-(3-methylsulfanyl-propyl)-10H-phenothiazine (108841-60-7)

N,N,N'-triethylethanediamine (105-04-4) + 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) → N,N,N'-triethyl-N'-(3-phenothiazin-10-yl-propyl)-ethylenediamine (104037-51-6)

10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + di-n-propylamine (142-84-7) → (3-phenothiazin-10-yl-propyl)-dipropyl-amine (97656-07-0)

10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + diethylamine (109-89-7) → chlorproethazine (47205-14-1)

Conditions	Yield
With copper

10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + diallylamine (124-02-7) → diallyl-(3-phenothiazin-10-yl-propyl)-amine (102446-63-9)

10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + nortropine (538-09-0) → 8-(3-phenothiazin-10-yl-propyl)-nortropane-3endo-ol (116105-78-3)

Conditions	Yield
With ethanol; sodium carbonate

10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) + 3-tropanol (120-29-6) → 3endo-hydroxy-8ξ-methyl-8ξ-(3-phenothiazin-10-yl-propyl)-nortropanium; chloride (119074-89-4)

4-(2-Hydroxyethyl)piperidine (622-26-4) + 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) → 2-[1-(3-phenothiazin-10-yl-propyl)-piperidin-4-yl]-ethanol (95129-41-2)

Conditions	Yield
With potassium carbonate; sodium iodide In butanone Heating;

octahydro-1H-pyrido[1,2-a]pyrazine (4430-75-5) + 10-(3-chloropropyl)-10H-phenothiazine (5909-59-1) → 10-[3-(octahydro-pyrido[1,2-a]pyrazin-2-yl)-propyl]-10H-phenothiazine (32418-83-0)

Conditions	Yield
at 100℃; for 18h;

Upstream product

• 632-02-0 3-chloropropyl p-toluenesulfonate 
• 109-72-8 n-butyllithium 
• 92-84-2 10H-phenothiazine 
• 109-70-6 1.3-chlorobromopropane 
• 3733-38-8 10-(3-piperidin-1-yl-propyl)-10H-phenothiazine 
• 76069-04-0 phenothiazine nitranion 
• 334990-68-0 [β-(10-Phenothiazyl)propoxy]phosphonic acid dichloride 
• 63397-92-2 3-(10H-phenothiazin-10-yl)propan-1-ol 
• 1698-80-2 10H-phenothiazine-10-propanenitrile 
• 362-03-8 3-(10H-phenothiazin-10-yl)propanoic acid 
• 107943-89-5 β-(10-Phenothiazyl)propionic acid ethyl ester 
• 4091-91-2 3-chloro-1-(10H-phenothiazin-10-yl)propan-1-one 
• 6940-76-7 1-iodo-3-chloro-propane 

Downstream Products

• 3733-38-8 10-(3-piperidin-1-yl-propyl)-10H-phenothiazine 
• 47205-14-1 chlorproethazine 
• 95129-41-2 1-<3-Phenothiazinyl-(10)-propyl>-4-<2-hydroxy-aethyl>-piperidin. 
• 32418-83-0 10-[3-(octahydro-pyrido[1,2-a]pyrazin-2-yl)-propyl]-10H-phenothiazine 
• 4047-13-6 1-(3-phenothiazin-10-yl-propyl)-4-phenyl-piperidine-4-carbonitrile 
• 14106-72-0 1-(3-phenothiazin-10-yl-propyl)-4-phenyl-piperidine-4-carboxylic acid ethyl ester 
• 123995-25-5 10-[3-(4-benzyl-piperazin-1-yl)-propyl]-10H-phenothiazine 
• 58-40-2 promazine 
• 58012-09-2 8-(3-phenothiazin-10-yl-propyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one 
• 1313585-48-6 tert-butyl 3-(10H-phenothiazin-10-yl)propyl(4-(2-perfluoroctylethyl)benzyloxy)carbamate 
• 1370649-65-2 1-[(3-nitrophenyl)methylidene]-3-[3-(10H-phenothiazin-10-yl)propyl]urea 
• 1370649-66-3 1-[(2-nitrophenyl)methylidene]-3-[3-(10H-phenothiazin-10-yl)propyl]urea 
• 1370649-67-4 1-[(4-methoxyphenyl)methylidene]-3-[3-(10H-phenothiazin-10-yl)propyl]urea 
• 1370649-68-5 1-[(4-methylphenyl)methylidene]-3-[3-(10H-phenothiazin-10-yl)propyl]urea 

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