Hydrochloric Acid → HCID 11510765, compound

HRID 908979Notes

Reaction equation

HRID 908979 reaction equation
CC(CC)=O.[CH3:6][N:7]([CH3:36])[C:8]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([NH:17][CH:18]([CH3:29])[CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:16])[CH2:10][CH2:9]1.C(NC1CCCCC1)(NC1CCCCC1)=O.[ClH:53]>C(O)C>[ClH:53].[CH3:36][N:7]([CH3:6])[C:8]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([NH:17][CH:18]([CH3:29])[CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:16])[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4277N,N'-DicyclohexylureaHCID 6569Methyl Ethyl KetoneHCID 11510766HCID 11510766, compound

Product 1

HCID 11510765HCID 11510765, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl methyl ketone (55 ml) was added to a mixture of 2-(4-dimethylamino-4-phenylcyclohexyl)-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide with dicyclohexylurea (939 mg) and the mixture was heated to 40° C. and filtered. The acetamide thereby remained as a colourless solid (327 mg, 0.78 mmol) with an m.p. of 198-200° C. It was dissolved in ethanol (20 ml), and 5 M propanolic hydrochloric acid (0.22 ml, 1.11 mmol) was added. After 2 h the reaction mixture was concentrated to 2 ml, ether (50 ml) was added and the mixture was stirred at RT for 1 h. It was possible to isolate the product as a colourless solid with an m.p. of 150-155° C. in a yield of 33% (338 mg).

Workup

  1. filtrationfiltered
  2. concentrationAfter 2 h the reaction mixture was concentrated to 2 ml, ether (50 ml)
  3. additionwas added

Sources & evidence

ORD record
ord-c5adcd204653420a8601449c01d72ffd
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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