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

HRID 1022370Notes

Reaction equation

HRID 1022370 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 thionylchloride are 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 is then heated up to 60° C. for 48 h. After cooling to 20° C., the solids are filtered and the filtrate is evaporated to give 13.2 g of 4-amino-1-methoxy-piperidine-4-carboxylic acid methyl ester hydrochloride as brown cristalline solid.

Workup

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

Sources & evidence

ORD record
ord-9f47c9f607e141558f22bd3df04c3fe1
Source dataset
uspto-grants-2014_05
Patent number
US08722578B2

Reaction notes

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