Methanol → Benzyl 4-amino-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate hydrochloride

HRID 64404Notes

Reaction equation

HRID 64404 reaction equation
[NH2:1][C:2]1([CH2:18][C:19]([OH:21])=[O:20])[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.S(Cl)([Cl:24])=O.[CH3:26]O>>[ClH:24].[NH2:1][C:2]1([CH2:18][C:19]([O:21][CH3:26])=[O:20])[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 54147179{4-Amino-1-[(benzyloxy)carbonyl]piperidin-4-yl}acetic acid

Product 1

HCID 86713411Benzyl 4-amino-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate hydrochloride

Procedure

To a suspension of 300 mg of {4-amino-1-[(benzyloxy)carbonyl]piperidin-4-yl}acetic acid in 6 ml of methanol was added 150 μl of thionyl chloride, followed by stirring for 2 days. The reaction mixture was concentrated under reduced pressure, ether was added thereto, and the resulting solid was collected by filtration and dried to obtain 350 mg of benzyl 4-amino-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate hydrochloride.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ether
  2. additionwas added
  3. filtrationthe resulting solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-e2aaf6dc0faa40a5aa5bf00f64422ee6
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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