Benzene → HCID 21428980, compound

HRID 437638Notes

Reaction equation

HRID 437638 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[C:6]([N:8]1[CH2:10][CH2:9]1)=[O:7])[CH3:2].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2([OH:28])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.C1C=CC=CC=1.CO>O(CC)CC>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2([OH:28])[CH2:23][CH2:24][N:25]([CH2:9][CH2:10][NH:8][C:6](=[O:7])[C:5]3[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=3[O:3][CH2:1][CH3:2])[CH2:26][CH2:27]2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 887MethanolHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 21428967HCID 21428967, compound

Product 1

HCID 21428980HCID 21428980, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.96 parts of 1-(2- ethoxybenzoyl)aziridine, 1.06 parts of 4-(4-chlorophenyl)-4-piperidinol, 5.4 parts of benzene and 0.8 parts of methanol is stirred and refluxed for 2 hours. The reaction mixture is cooled. Upon the addition of 1,1'-oxybisethane, the product is precipitated. It is filtered off, crystallized from 2-propanol, filtered off again and dried overnight in vacuo at 80° C, yielding 1.4 parts of N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-2-ethoxybenzamide; mp. 171°-173° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe product is precipitated
  4. filtrationIt is filtered off
  5. customcrystallized from 2-propanol
  6. filtrationfiltered off again
  7. customdried overnight in vacuo at 80° C

Sources & evidence

ORD record
ord-37d5e5e8329f4f0e89ade5e40842826a
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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