4-Phenylcyclohexylamine → HCID 70158585, compound

HRID 990693Notes

Reaction equation

HRID 990693 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH2:13]([O:15][C:16](=[O:25])[CH:17]([CH:22]([CH3:24])[CH3:23])[CH2:18][C:19]([OH:21])=O)[CH3:14].[C:26]1([CH:32]2[CH2:37][CH2:36][CH:35]([NH2:38])[CH2:34][CH2:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:13]([O:15][C:16](=[O:25])[CH:17]([CH2:18][C:19](=[O:21])[NH:38][CH:35]1[CH2:34][CH2:33][CH:32]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:37][CH2:36]1)[CH:22]([CH3:24])[CH3:23])[CH3:14]

Participants

6

Reactant 3

HCID 298974-PhenylcyclohexylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9815473HCID 9815473, compound

Product 1

HCID 70158585HCID 70158585, compoundYield 26.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.80 g) was added to a solution of 4-dimethylaminopyridine (0.04g) and Intermediate 10 (0.54 g) in dichloromethane (30 ml) and the solution was stirred for 30 min, then a solution of Intermediate 14 (0.50 g) in dichloromethane (5 ml) was added and the mixture was stirred overnight. The solvent was removed in vacuo and the resulting slurry dissolved in ethyl acetate (100 ml), washed with water (10 ml), aqueous sodium bicarbonate (10 ml) and brine (10 ml), dried over magnesium sulphate (1 g) and the solvent removed in vacuo. The resulting oil was purified by flash chromatography (silica, eluent 30% ethyl acetate/hexane) to yield the title compound as a yellow solid (0.26 g).

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe solvent was removed in vacuo
  3. dissolutionthe resulting slurry dissolved in ethyl acetate (100 ml)
  4. washwashed with water (10 ml), aqueous sodium bicarbonate (10 ml) and brine (10 ml)
  5. dry with materialdried over magnesium sulphate (1 g)
  6. customthe solvent removed in vacuo
  7. customThe resulting oil was purified by flash chromatography (silica, eluent 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a218783cfd0545b6a0aea828b55a2280
Source dataset
uspto-grants-2002_10
Patent number
US06462042B1

Reaction notes

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