• Name

  1,1-Cyclohexanediacetic acid mono amide

• EINECS 449-430-4
• CAS No. 99189-60-3
• Article Data11
• CAS DataBase
• Density 1.135 g/cm³
• Solubility
• Melting Point 143-146 °C
• Formula C₁₀H₁₇NO₃
• Boiling Point 443.6 °C at760mmHg
• Molecular Weight 199.25
• Flash Point 222.1 °C
• Transport Information
• Appearance White powder
• Safety 22-24/25
• Risk Codes 61
• Molecular Structure
• Hazard Symbols T
• Synonyms Cyclohexaneaceticacid, 1-(carbamoylmethyl)- (6CI);1,1-Cyclohexanediacetic acid monoamide;1-(Carboxymethyl)cyclohexane-1-acetamide;1-[(Aminocarbonyl)methyl]cyclohexaneacetic acid;
• PSA 80.39000
• LogP 1.98730

Synthetic route

1130-32-1

3-azaspiro[5,5]undecane-2,4-dione

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

Conditions

Conditions	Yield
With water; sodium hydroxide at 50℃; for 6h; Reagent/catalyst;	93%
With sodium hydroxide
Stage #1: 3-azaspiro[5.5]undecane-2,4-dione With sodium hydroxide; water at 95 - 105℃; for 6h; Heating / reflux; Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20 - 40℃; for 1h; pH=6.5; Industry scale; Stage #3: With hydrogenchloride In water; isopropyl alcohol at 35 - 40℃; for 1h; pH=4.0 - 4.5; Industry scale;
Stage #1: 3-azaspiro[5.5]undecane-2,4-dione With sodium hydroxide; water for 1h; Heating / reflux; Stage #2: With hydrogenchloride In water at 25℃; pH=5;

90961-78-7

spiro[cyclohexane-1,9’-(3,7-diazabicycle-[3.3.1]nonane)]-2’,4’,6’,8’-tetraone

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

Conditions

Conditions	Yield
With water; sodium hydroxide at 100 - 105℃; for 18h;	80.8%

1010-26-0

1,1-cyclohexanediacetic acid anhydride

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

Conditions

Conditions	Yield
Stage #1: 1,1-cyclohexanediacetic acid anhydride With ammonia In water; acetic acid; toluene at 10 - 30℃; for 1.33333h; pH=> 8; Stage #2: With hydrogenchloride In water at 40 - 45℃; for 0.333333h; pH=3.8 - 4.2;
Stage #1: 1,1-cyclohexanediacetic acid anhydride With sodium hydroxide; water; ammonium chloride at 0 - 30℃; for 4h; Stage #2: With hydrogenchloride; water pH=2 - 3; Product distribution / selectivity;
Stage #1: 1,1-cyclohexanediacetic acid anhydride With ammonia; water In isopropyl alcohol at 5℃; for 1h; Stage #2: With hydrogenchloride; water In isopropyl alcohol at 15 - 20℃; for 15h; pH=2 - 3; Product distribution / selectivity;

4355-11-7

1,1-cyclohexanediacetic acid

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetic anhydride / 2 h / 130 °C 2.1: ammonia / benzene / 5 h / 25 - 105 °C 2.2: 1.5 h / 55 °C / pH 4 View Scheme
Multi-step reaction with 2 steps 1: acetic anhydride / 0.5 h / 110 °C 2: ammonium hydroxide / 1 h View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

64744-50-9

gabapentin-lactam

Conditions

Conditions	Yield
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at 0 - 40℃; for 3.5h; Stage #2: With hydrogenchloride In water at 100 - 105℃; for 3h; pH=8.2 - 8.8; Product distribution / selectivity; Heating / reflux;	100%
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at 0 - 50℃; for 3h; Stage #2: With hydrogenchloride In water at 100 - 105℃; for 3h; pH=11 - 12; Product distribution / selectivity;	93.8%
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide In water at 20 - 30℃; for 0.5h; Stage #2: With sode de l'acide trichloroisocyanurique In water at 0 - 20℃; for 5h; Stage #3: In water; toluene at 80℃; for 8h; Reagent/catalyst;	85%
Multi-step reaction with 2 steps 1.1: trichloroisocyanuric acid / methanol / 1.75 h / 20 - 25 °C 2.1: sodium hydroxide / water / 4 h / 0 - 20 °C 2.2: 8 h / 80 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

C10H16ClNO3

Conditions

Conditions	Yield
With trichloroisocyanuric acid In methanol at 20 - 25℃; for 1.75h;	100%

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

63562-00-5

1-(aminomethyl)-1-cyclohexaneacetic acid sodium salt

Conditions

Conditions	Yield
With sodium hypobromide; sodium hydroxide In water at 40 - 55℃; Reagent/catalyst; Temperature; Hofmann Rearrangement; Flow reactor;	91.98%
With sodium hydroxide; sodium hypobromide In water at 0 - 10℃; for 2 - 3h; Product distribution / selectivity; Hofmann Rearrangement;	67%
With sodium hydroxide; sodium hypochlorite In water at 0 - 10℃; for 2 - 3h; Product distribution / selectivity; Hofmann Rearrangement;	65%

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1-(aminomethyl)cyclohexaneacetic acid hydrochloride

Conditions

Conditions	Yield
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at -5 - 25℃; for 9h; Stage #2: With hydrogenchloride In water; butan-1-ol pH=1.5;	75%
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; bromine In water at -8 - 40℃; for 2h; Stage #2: With hydrogenchloride; water for 4h; pH=2;
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 0.5 h / 20 - 30 °C 1.2: 5 h / 0 - 20 °C 1.3: 8 h / 80 °C 2.1: hydrogenchloride; water / 10 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1.1: trichloroisocyanuric acid / methanol / 1.75 h / 20 - 25 °C 2.1: sodium hydroxide / water / 4 h / 0 - 20 °C 2.2: 8 h / 80 °C 3.1: hydrogenchloride; water / 10 h / 100 °C View Scheme
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hypochlorite; sodium hydroxide In water; benzene at 100℃; Stage #2: at 95℃; for 3h; Temperature;

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

gabapentin hemisulphate

Conditions

Conditions	Yield
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at -5 - 25℃; for 9h; Stage #2: With sulfuric acid In water; butan-1-ol pH=1.5;	73.8%

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

60142-96-3

H-Gpn-OH

Conditions

Conditions	Yield
With sodium carbonate In benzyl alcohol pH=7 - 7.5; Product distribution / selectivity;	68.6%
With sodium hydroxide; sodium hypochlorite In water at -10 - 20℃; for 8h; Hofmann Rearrangement;
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hypochlorite; sodium hydroxide In water at 40℃; Hofmann Rearrangement; Stage #2: With sodium metabisulfite In water Product distribution / selectivity;

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-02-4

2-(1-((methyleneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-03-5

2-(1-((ethylideneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-04-6

2-(1-((benzylideneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-05-7

2-(1-((4-methoxybenzylideneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-06-8

2-(1-((2-hydroxybenzylideneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-08-0

2-(1-((2-chloro-6-fluorobenzylideneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-09-1

2-(1-((2-chlorobenzylideneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-10-4

2-(1-((4-fluorobenzylideneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-11-5

2-(1-((4-ethoxybenzylideneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-12-6

2-(1-(((pyridin-2-yl)methyleneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-13-7

2-(1-((1-(4-ethoxyphenyl)ethylideneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-14-8

2-(1-((1-(pyridin-2-yl)ethylideneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-15-9

C18H22N2O2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

2-(1-((1-(1H-indol-3-yl)ethylideneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-17-1

2-(1-((1-(pyridin-3-yl)ethylideneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1262837-18-2

2-(1-((1-(naphthalen-2-yl)ethylideneamino)methyl)cyclohexyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hypobromide; sodium hydroxide / 15 h / 55 °C 2: sulfuric acid / ethanol / 20 °C View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

gabapentin oxalate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hypochlorite; sodium hydroxide / benzene; water / 100 °C 1.2: 3 h / 95 °C 2.1: 2 h / pH 5 View Scheme

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

Reaxys ID: 34429109

Reaxys ID: 34429109

Conditions

Conditions	Yield
With alkali metal hypohalogenate Hofmann Rearrangement;

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1121-89-7

piperidine-2,6-dione

Conditions

Conditions	Yield
With acetic acid In toluene at 70℃; for 6h; Temperature;

1,1-Cyclohexanediacetic acid mono amide Chemical Properties

1,1-Cyclohexanediacetic acid mono amide Safety Profile

1,1-Cyclohexanediacetic acid mono amide Specification