Methanol → 4-Amino-1-methoxy-piperidine-4-carboxylic acid methyl ester hydrochloride

HRID 1962358Notes

Reaction equation

HRID 1962358 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C:6]1([C:14]([OH:16])=[O:15])[CH2:11][CH2:10][N:9]([O:12][CH3:13])[CH2:8][CH2:7]1.[CH3:17]O>>[ClH:3].[CH3:17][O:15][C:14]([C:6]1([NH2:5])[CH2:11][CH2:10][N:9]([O:12][CH3:13])[CH2:8][CH2:7]1)=[O:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 596145764-Amino-1-methoxy-piperidine-4-carboxylic acid

Product 1

HCID 666317834-Amino-1-methoxy-piperidine-4-carboxylic acid methyl ester hydrochloride

Conditions

Temperature
60 °C

Procedure

25.7 g of thionyl chloride was added at a temperature of 0-10° C. within 40 minutes to a suspension of 12.5 g of 4-amino-1-methoxy-piperidine-4-carboxylic acid in 100 ml of methanol. The reaction mixture was then heated up to 60° C. for 48 h. After cooling to 20° C., the solids were filtered and the filtrate was evaporated to give 13.2 g of 4-amino-1-methoxy-piperidine-4-carboxylic acid methyl ester hydrochloride salt as a brown crystalline solid, mp: 198° C.

Workup

  1. temperatureAfter cooling to 20° C.
  2. filtrationthe solids were filtered
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-f5d124dbd4aa448a80c509bdc9f396a8
Source dataset
uspto-grants-2013_04
Patent number
US08415369B2

Reaction notes

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