Sodium Hydroxide → 4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl alcohol

HRID 263733Notes

Reaction equation

C([O:4][CH2:5][CH2:6][CH:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:37])[CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23]([OH:36])([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[CH:9][C:8]1([CH3:39])[CH3:38])(=O)C.[OH-].[Na+]>CO>[OH:36][C:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH:20]1[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][CH2:14][C:13]([C:10]2[CH:11]=[CH:12][CH:7]([CH2:6][CH2:5][OH:4])[C:8]([CH3:39])([CH3:38])[CH:9]=2)=[O:37])[CH2:18][CH2:19]1

Participants

Conditions

Temperature: 68 °C

Procedure

Dissolve 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl acetate (69.0 g, 0.131 mol) in methanol (2.5 L) and add 10% aqueous sodium hydroxide (769 mL, 1.92 mol). Stir at reflux for 1.5 hours, cool to 68° C. and evaporate the solvent in vacuo to a residue (700 mL). Add chloroform (1 L) and stir until solids are dissolved. Separate the organic phase and extract the aqueous phase with chloroform (3×300 mL). Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo and recrystallize (toluene) to give the title compound as a cream-colored powder; mp 135°-137° C.

Workup

temperatureat reflux for 1.5 hours
customevaporate the solvent in vacuo to a residue (700 mL)
stirringAdd chloroform (1 L) and stir until solids
dissolutionare dissolved
customSeparate the organic phase
extractionextract the aqueous phase with chloroform (3×300 mL)
dry with materialCombine the organic phases, dry (MgSO4)
customevaporate the solvent in vacuo
customrecrystallize (toluene)

Sources & evidence

ORD record: ord-00bf93b3aa4f4706b923472427904f9a
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05644061

Reaction notes

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