Water → 3-[2-(4-Anilinocarbonylmethylamino-1-piperidyl) ethyl]indole

HRID 442481Notes

Reaction equation

HRID 442481 reaction equation
O.[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[CH2:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30].O>CN(C)C=O>[NH:31]([C:29]([CH2:28][NH:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH2:5][CH2:4]1)=[O:30])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11485ChloroacetanilideHCID 203843533-[2-(4-Aminopiperidyl)ethyl]indole, hydrate

Product 1

HCID 542686533-[2-(4-Anilinocarbonylmethylamino-1-piperidyl) ethyl]indoleYield 109.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[2-(4-Amino-1-piperidyl) ethyl]indole hydrate (1.31g.) was dissolved in dimethylformamide (15 ml) containing triethylamine (2 ml) and chloroacetanilide (0.85g) added. The mixture was stirred for 24 hours, poured into water (100 ml) and extracted with chloroform (2 × 50 ml). The combined chloroform layers were washed with water, dried (MgSO4), filtered and evaporated to give the title compound as an amber oil (2.06 g). This was converted to the hydrochloride (1.29 g), m.p. 240.7°, on addition of EtOH-HC1 and Et2O.

Workup

  1. additionadded
  2. extractionextracted with chloroform (2 × 50 ml)
  3. washThe combined chloroform layers were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-02982ff8c946439b80372bd23b5e340d
Source dataset
uspto-grants-1977_08
Patent number
US04045566

Reaction notes

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