Hydrochloric Acid → 4-(2,3-Dimethoxybenzoyl)piperidine hydrochloride

HRID 51280Notes

Reaction equation

HRID 51280 reaction equation
[CH3:1][O:2][C:3]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:4]=1[C:5]([CH:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]1)=[O:6].[ClH:26]>O1CCCC1>[ClH:26].[CH3:1][O:2][C:3]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:4]=1[C:5]([CH:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1)=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46780868N-Boc-(2,3-dimethoxyphenyl)-4-piperidinylmethanone2×

Product 1

HCID 227378634-(2,3-Dimethoxybenzoyl)piperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 25-mL three-neck flask equipped with a thermowell with a thermocouple, a reflux condenser, a stopper, and a magnetic stir bar was placed 4-(2,3-dimethoxybenzoyl)-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester (7) (1.1 g, 3.0 mmol) and 9.7 g of tetrahydrofuran. After 4-(2,3-dimethoxybenzoyl)-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester (7) had dissolved, 6.3 g of 3N aqueous hydrochloric acid was added in one portion. The reaction was stirred to 18 hours at ambient temperature and then heated to 60° C. for 4 hours to give 4-(2,3-dimethoxybenzoyl)piperidine hydrochloride.

Workup

  1. customInto a 25-mL three-neck flask equipped with a thermowell with a thermocouple, a reflux condenser
  2. temperatureheated to 60° C. for 4 hours

Sources & evidence

ORD record
ord-deca3b2ce48748ba956f49ef7552dbc0
Source dataset
uspto-grants-2004_03
Patent number
US06713627B2

Reaction notes

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