Dicyclohexylcarbodiimide → 2-(4-Dimethylamino-4-phenylcyclohexyl)-N-[2-(1H-indol-3-yl)ethyl]acetamide

HRID 908962Notes

Reaction equation

HRID 908962 reaction equation
Cl.[CH3:2][N:3]([CH3:20])[C:4]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8][CH:7]([CH2:10][C:11]([OH:13])=O)[CH2:6][CH2:5]1.C1(N=[C:28]=[N:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:20][N:3]([CH3:2])[C:4]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:5][CH2:6][CH:7]([CH2:10][C:11]([NH:3][CH2:4][CH2:5][C:6]2[C:31]3[C:30](=[CH:35][CH:34]=[CH:33][CH:32]=3)[NH:29][CH:28]=2)=[O:13])[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 673861314-Dimethylamino-4-phenylcyclohexyl-acetic acid hydrochloride

Product 1

HCID 115394472-(4-Dimethylamino-4-phenylcyclohexyl)-N-[2-(1H-indol-3-yl)ethyl]acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(4-dimethylamino-4-phenylcyclohexyl)acetic acid hydrochloride (298 mg, 1.0 mmol) in dry dimethylformamide under argon. The clear solution was cooled in an ice-bath and dicyclohexylcarbodiimide (417 mg, 2.0 mmol) was added. The reaction mixture was stirred at RT for 3 d and worked up by separating off the urea which had precipitated out and introducing the filtrate into a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml). The mixture was diluted with water, 5 M sodium hydroxide solution (4 ml, 20 mmol) was added and the mixture was stored at 5° C. for 16 h. The crude product thereby precipitated out as a beige-coloured substance (400 mg). After purification by chromatography on silica gel with methanol, the product was obtained as a beige-coloured solid in a yield of 35% (144 mg) and with an m.p.

Workup

  1. temperatureThe clear solution was cooled in an ice-bath
  2. customby separating off the urea which
  3. customhad precipitated out
  4. additionintroducing the filtrate
  5. additioninto a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml)
  6. additionwas added
  7. waitthe mixture was stored at 5° C. for 16 h
  8. customThe crude product thereby precipitated out as a beige-coloured substance (400 mg)
  9. customAfter purification by chromatography on silica gel with methanol
  10. customthe product was obtained as a beige-coloured solid in a yield of 35% (144 mg) and with an m.p.

Sources & evidence

ORD record
ord-037ec87b29b74a35a1aa2e78728dd51e
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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