N-4-Piperidylbenzamide → 1-[1-(4-Acetamidophenoxy)-2-hydroxyprop-3-yl]-4-benzamidopiperidine

HRID 437223Notes

Reaction equation

HRID 437223 reaction equation
[O:1]1[CH2:15][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1.[C:16]([NH:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)(C)C>[C:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:15][N:28]2[CH2:29][CH2:30][CH:25]([NH:24][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:26][CH2:27]2)=[CH:6][CH:7]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 118120N-4-PiperidylbenzamideHCID 2798712N-(4-((oxiran-2-yl)methoxy)phenyl)acetamide

Product 1

HCID 214305571-[1-(4-Acetamidophenoxy)-2-hydroxyprop-3-yl]-4-benzamidopiperidine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2,3-epoxy-1-(4-acetamidophenoxy)-propane (5.18 g. and 4 -benzamidopiperidine (6.13 g.) in isopropanol (250 ml.) was refluxed for 24 hours, cooled and a white crystalline solid was filtered off (8.90 g.). This was recrystallised from isopropanol to give 7.41 g. of the title compound as a quarter hydrate, m.p. 226°-8° C. (Found: C, 66.35; H, 7.1; N, 10.1. C23H29N3O4.1/4H2O requires C, 66.4; H, 7.15; N, 10.1%).

Workup

  1. temperaturecooled
  2. filtrationa white crystalline solid was filtered off (8.90 g.)
  3. customThis was recrystallised from isopropanol
  4. customto give 7.41 g

Sources & evidence

ORD record
ord-428508a1a3024595982b7ab62011906c
Source dataset
uspto-grants-1977_06
Patent number
US04029801

Reaction notes

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