Indole-3-Carboxylic Acid → (1-Benzyl-4-piperidyl)methyl indole-3-carboxylate

HRID 609593

Reaction equation

HRID 609593 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26]O)[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH2:26][CH:23]2[CH2:22][CH2:21][N:20]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:25][CH2:24]2)=[O:11])=[CH:2]1

Participants

3

Reactant 2

HCID 69867Indole-3-Carboxylic AcidHCID 736802(1-Benzylpiperidin-4-yl)methanol

Product 1

HCID 19599412(1-Benzyl-4-piperidyl)methyl indole-3-carboxylateYield 88%

Procedure

Indole-3-carboxylic acid was converted to its acid chloride and then reacted with 1-benzyl-4-piperidinemethanol (D7) using the method given in Example 1a. The resulting orange oil was chromatographed on silica gel eluting with chloroform/ethanol (9:1) to afford (1-benzyl-4-piperidyl)methyl indole-3-carboxylate as a yellow oil (88%)

Workup

  1. customThe resulting orange oil was chromatographed on silica gel eluting with chloroform/ethanol (9:1)

Sources & evidence

ORD record
ord-7fbd3c741116489abdb6755e5ccd7147
Source dataset
uspto-grants-1999_12
Patent number
US05998409

Linked notes

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