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

HRID 1984877Notes

Reaction equation

HRID 1984877 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]>CCOC(C)=O>[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

4

Reactant 2

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

Product 1

HCID 45072217Benzyl (piperidin-4-ylmethyl)carbamate hydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-(benzyloxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester (10.2 g, 29.3 mmol) in EtOAc (100 mL) was cooled on an ice-bath and 4 M hydrogen chloride in EtOAc (100 mL) was added. The mixture was stirred at ambient temperature for 1 hr and concentrated. The residue was suspended in hexane (30 mL) and the mixture was stirred at ambient temperature for 30 min. The solid was collected by filtration, washed with hexane, and dried under reduced pressure to give piperidin-4-ylmethyl-carbamic acid benzyl ester hydrochloride (7.24 g, 87%) as a white solid.

Workup

  1. concentrationconcentrated
  2. stirringthe mixture was stirred at ambient temperature for 30 min
  3. filtrationThe solid was collected by filtration
  4. washwashed with hexane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-d8515f42c03f49d2892cade5be2fad9c
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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