1,4-Dioxane hydrochloride → 4-(2-Bromo-5-methoxybenzyl)piperidine hydrochloride

HRID 1006056Notes

Reaction equation

HRID 1006056 reaction equation
[ClH:1].O1CCOCC1.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=2[Br:30])[CH2:17][CH2:16]1)=O)(C)(C)C>C(O)(=O)C>[ClH:1].[Br:30][C:23]1[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:22]=1[CH2:21][CH:18]1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 226753254-(2-Bromo-5-methoxybenzyl)-1-Boc-piperidine

Product 1

HCID 226753344-(2-Bromo-5-methoxybenzyl)piperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

At room temperature, 4N-hydrogen chloride/dioxane (35 mL) was added dropwise to a solution of the crude product (18.3 g) of N-tert-butoxycarbonyl-4-(2-bromo-5-methoxy-benzyl)piperidine in acetic acid (50 mL), and the resulting mixture was stirred at 60° C. for 1 hour. The solvent was distilled off and ethyl acetate was added to the residue to effect crystallization. The crystals were collected by filtration, washed with ethyl acetate and then dried to obtain 12.9 g (40.2 mmol) of 4-(2-bromo-5-methoxybenzyl)piperidine hydrochloride.

Workup

  1. distillationThe solvent was distilled off
  2. additionethyl acetate was added to the residue
  3. customcrystallization
  4. filtrationThe crystals were collected by filtration
  5. washwashed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-b5e648d60a1640dba85706c5beaba40e
Source dataset
uspto-grants-2004_09
Patent number
US06787560B2

Reaction notes

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