Sodium Sulfate → 1-Benzyl-4-(phenylamino)piperidine-4-methanol

HRID 1380958Notes

Reaction equation

HRID 1380958 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:14](OC)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:14][OH:15])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24436Sodium SulfateHCID 2724430Methyl 1-benzyl-4-(phenylamino)piperidine-4-carboxylate

Product 1

HCID 30172301-Benzyl-4-(phenylamino)piperidine-4-methanolYield 104.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

A stirred solution of 76.1 g of methyl 1-benzyl-4-anilino-4-piperidine carboxylate in 1200 ml of toluene is maintained at ambient temperature while 130 ml of a 70% solution of sodium dihydrobis(2-methoxyethoxy)aluminate in benzene is added dropwise. Stirring is continued for one hour after the addition. Two hundred grams of a saturated solution of sodium sulfate is added. The aqueous portion is removed and the organic portion is dried over sodium sulfate and flash evaporated to give 72.5 g of 1-benzyl-4-anilino-4-piperidinemethanol, as an oil.

Workup

  1. additionis added dropwise
  2. additionafter the addition
  3. customThe aqueous portion is removed
  4. dry with materialthe organic portion is dried over sodium sulfate and flash
  5. customevaporated

Sources & evidence

ORD record
ord-ea8e16334bbb4aa5b0dbcd36acebbcb3
Source dataset
uspto-grants-1986_04
Patent number
US04584303

Reaction notes

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