Hydrochloric Acid → 3-Benzylpiperidine hydrochloride

HRID 395360Notes

Reaction equation

HRID 395360 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1)=O)(C)(C)C.[ClH:21]>CO.O1CCOCC1>[ClH:21].[CH2:14]([CH:10]1[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22351199Tert-butyl 3-benzylpiperidine-1-carboxylate

Product 1

HCID 161878763-Benzylpiperidine hydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-(t-butoxycarbonyl)-3-benzylpiperidine (400 mg, 1.45 mmol) in methanol (5 mL) was added hydrogen chloride in dioxane (4M, 15 mL). The resulting yellow solution was stirred for 1 hr, at which time the reaction was concentrated in vacuo to provide 3-benzylpiperidine hydrochloride (308 mg, 100%) as an amorphous solid. 1H NMR (300 MHz, CD3OD), δ: 7.27 (m, 2H,), 7.19 (m, 3H), 3.29 (br. d, 1H, J=12 Hz), 3.20 (br. d, 1H, J=12 Hz), 2.87 (br. t, 1H, J=12 Hz), 2.67 (m, 1H), 2.60 (d, 2H, J=7 Hz), 2.08 (m, 1H) 1.70-1.87 (m, 3H), 1.26 (m, 1H). MS (CI), m+/z: (M+H)+=176.

Workup

  1. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-387f9ea230744311bfaa37ed600b80e0
Source dataset
uspto-grants-2003_08
Patent number
US06605623B1

Reaction notes

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