Hydrochloric Acid → 2-(4-Dimethylamino-4-phenylcyclohexyl)-N-[6-(1H-indol-3-yl)hexyl]acetamide hydrochloride

HRID 908978Notes

Reaction equation

HRID 908978 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)=[O:11])[CH2:5][CH2:4]1.[ClH:35]>CC(CC)=O.C(O)C>[ClH:35].[CH3:34][N:2]([CH3:1])[C:3]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)=[O:11])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 116129622-(4-Dimethylamino-4-phenylcyclohexyl)-N-[6-(1H-indol-3-yl)hexyl]acetamide

Product 1

HCID 116129612-(4-Dimethylamino-4-phenylcyclohexyl)-N-[6-(1H-indol-3-yl)hexyl]acetamide hydrochlorideYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-(4-Dimethylamino-4-phenylcyclohexyl)-N-[6-(1H-indol-3-yl)hexyl]acetamide (516 mg, 1.12 mmol) was dissolved in a mixture of ethyl methyl ketone (25 ml) and ethanol (5 ml), and 5 M isopropanolic hydrochloric acid (0.44 ml, 2.2 mmol) was added. After 3 h the reaction mixture was concentrated, ether (15 ml) was added and the mixture was concentrated again. The residue was digested with ether (30 ml). After filtration, the product was obtained as a beige-coloured solid in a yield of 62% (342 mg).

Workup

  1. additionwas added
  2. concentrationAfter 3 h the reaction mixture was concentrated
  3. additionether (15 ml) was added
  4. concentrationthe mixture was concentrated again
  5. filtrationAfter filtration
  6. customthe product was obtained as a beige-coloured solid in a yield of 62% (342 mg)

Sources & evidence

ORD record
ord-6c8b986d440341758fdbcabc423f99f3
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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