Diketene → acetoacetic acid-N-benzyl-2-piperidinylmethyl ester

HRID 544257Notes

Reaction equation

HRID 544257 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]=[C:17]1[O:21][C:19](=[O:20])[CH2:18]1>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][O:15][C:19](=[O:20])[CH2:18][C:17]([CH3:16])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 12661DiketeneHCID 2735486(1-Benzylpiperidin-2-yl)methanol

Product 1

HCID 20459843acetoacetic acid-N-benzyl-2-piperidinylmethyl esterYield 70%

Procedure

Then, 10.0 g of the 1-benzyl-2-piperidine methanol and 4.30 g of diketene were reacted similarly as in Reference Example 1, and the reaction product was purified by silica gel column chromatography (eluent:chloroform:methanol=9:1 v/v), to obtain 9.86 g of acetoacetic acid-N-benzyl-2-piperidinylmethyl ester (yield: 69.9%). This was used in the reaction of Example 5 without distillation.

Workup

  1. customthe reaction product was purified by silica gel column chromatography (eluent:chloroform:methanol=9:1 v/v)

Sources & evidence

ORD record
ord-06f123e0321f45c9ba29a667b41e43b2
Source dataset
uspto-grants-1984_05
Patent number
US04448964

Reaction notes

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