Benzoyl chloride → HCID 86629950, compound

HRID 539420Notes

Reaction equation

HRID 539420 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([NH2:8])[CH:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH:9]([C@@H:5]1[CH2:4][CH2:3][C@@H:2]([CH3:1])[CH2:7][C@@H:6]1[NH:8][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:11])[CH3:10].[CH:9]([C@H:5]1[CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:7][C@H:6]1[NH:8][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 7412Benzoyl chlorideHCID 89497Cyclohexanamine, 5-methyl-2-(1-methylethyl)-3×

Product 1

HCID 86629950HCID 86629950, compound

Procedure

The aforementioned product is obtained as a colorless solid containing in total 97.6% of the desired neomenthylamine derivatives from racemic neomenthylamine, as in the GP, by reaction with benzoylchloride. Furthermore, two further isomeric menthylamine derivatives are present at 1.3% and 1.0%, corresponding to a purity of isomeric N-(-2-isopropyl-5-methylcyclohexyl)benzamides of 99.9%.

Workup

  1. customThe aforementioned product is obtained as a colorless solid

Sources & evidence

ORD record
ord-d4e23fa94d804d059430b2cce77fc5f3
Source dataset
uspto-grants-2014_10
Patent number
US08871288B2

Reaction notes

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