1-[(3,4-Dichlorophenyl)methyl]piperidin-4-amine → N-(2-{3-[1-(3,4-Dichloro-benzyl)-piperidin-4-ylamino]-2-hydroxy-propoxy}-phenyl)-benzamide

HRID 1072502Notes

Reaction equation

HRID 1072502 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:25][N:26]1[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]1>>[Cl:21][C:22]1[CH:23]=[C:24]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:25][N:26]1[CH2:27][CH2:28][CH:29]([NH:32][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:30][CH2:31]1

Participants

3

Reactant 2

HCID 109781561-[(3,4-Dichlorophenyl)methyl]piperidin-4-amineHCID 22386962N-(2-Oxiranylmethoxy-phenyl)-benzamide

Product 1

HCID 10119159N-(2-{3-[1-(3,4-Dichloro-benzyl)-piperidin-4-ylamino]-2-hydroxy-propoxy}-phenyl)-benzamide

Conditions

Temperature
77.5 °C

Procedure

To a solution of N-(2-Oxiranylmethoxy-phenyl)-benzamide (0.2 ml, 0.1M in DMSO) was added (0.2 ml, 0.1M in EtOH) of 1-(3,4-Dichloro-benzyl)-piperidin-4-ylamine. The resulting mixture was heated at 75-80° C. for 24 hours. The ethanol was removed and the product was purified with preparative LC/MS.

Workup

  1. customThe ethanol was removed
  2. customthe product was purified with preparative LC/MS

Sources & evidence

ORD record
ord-e2eb10ff0d72400caa470575bba00bdd
Source dataset
uspto-grants-2005_06
Patent number
US06911458B2

Reaction notes

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