Methanol → N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-4-fluoro-2-methoxybenzamide

HRID 437643Notes

Reaction equation

HRID 437643 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]2[CH2:10][CH2:9]2)=[O:7])=[C:4]([O:13][CH3:14])[CH:3]=1.[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.CO>C1C=CC=CC=1>[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][C:2]([F:1])=[CH:3][C:4]=3[O:13][CH3:14])[CH2:26][CH2:27]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 214288101-(4-Fluoro-2-methoxybenzoyl)-aziridine

Product 1

HCID 21428912N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-4-fluoro-2-methoxybenzamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 8 parts of 1-(4-fluoro-2-methoxybenzoyl)-aziridine, 3.7 parts of 4-(4-chlorophenyl)-4-piperidinol, 54 parts of benzene and 8 parts of methanol is stirred and refluxed for 1.50 hours. The reaction mixture is cooled to room temperature and 90 parts of benzene are added. The whole is washed with water and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is crystallized from 2-propanone. The product is filtered off and dried, yielding 3.5 parts of N-{2-[4-(4-chlorophenyl)-4- hydroxy-1-piperidinyl]ethyl}-4-fluoro-2-methoxybenzamide; mp. 156.7° C.

Workup

  1. temperaturerefluxed for 1.50 hours
  2. washThe whole is washed with water
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from 2-propanone
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-aeb82255fe8c4d2c96ef77630cd006d3
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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