Hydrochloric Acid → Benzyl (piperidin-4-ylmethyl)carbamate hydrochloride

HRID 854301Notes

Reaction equation

HRID 854301 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:26]>O1CCOCC1.CCOCC>[ClH:26].[CH2:19]([O:18][C:16](=[O:17])[NH:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 117920261-N-Boc-4-(N-cbz-aminomethyl)piperidine

Product 1

HCID 45072217Benzyl (piperidin-4-ylmethyl)carbamate hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 35 g of 4-(benzyloxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester and 50 mL of 4N HCl in dioxane was stirred at rt for 3 h, then diluted with 200 mL of ether and filtered. The piperidin-4-ylmethyl-carbamic acid benzyl ester hydrochloride salt was obtained as a white fluffy solid. The free base was obtained by partitioning the hydrochloride between 50 mL chloroform and 50 mL saturated aqueous Na2CO3.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-f3afd1b4c0234bfa872347379dbdd1c9
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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