Methyl Isobutyl Ketone → Ethyl 4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzoate

HRID 484496Notes

Reaction equation

HRID 484496 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:15][CH2:14][C:11]3([O:13][CH2:12]3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:16][C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CC(C)CC(=O)C>O>[OH:13][C:11]1([CH2:12][O:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=2)[CH2:14][CH2:15][N:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 892386-Benzyl-1-oxa-6-azaspiro(2,5)octane

Product 1

HCID 14989213Ethyl 4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzoateYield 41.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 37.5 parts of 6-(phenylmethyl)-1-oxa-6-azaspiro[2.5]octane, 24.9 parts of ethyl 4-hydroxybenzoate, 20.7 parts of potassium carbonate and 200 parts of 4-methyl-2-pentanone was stirred overnight at reflux temperature. After cooling, water was added. The precipitated product was filtered off, washed with water and crystallized from 1,1'-oxybisethane. The product was filtered off and dried, yielding 23 parts (41.5%) of ethyl 4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzoate; mp. 100.2° C. (int. 78).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationThe precipitated product was filtered off
  4. washwashed with water
  5. customcrystallized from 1,1'-oxybisethane
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-3a71ccaf6eb74629a544733195621d5c
Source dataset
uspto-grants-1993_07
Patent number
US05231184

Reaction notes

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