HCID 69670020, compound → HCID 69669886, compound

HRID 1623218Notes

Reaction equation

HRID 1623218 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[OH:22]>Cl.CO>[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)=[CH:4][C:3]=1[OH:22]

Participants

4

Reactant 1

HCID 69670020HCID 69670020, compound

Product 1

HCID 69669886HCID 69669886, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-(4-bromo-3-hydroxybenzyl)piperidine-1-carboxylate (4-5-1) (1.20 g, 3.2 mmol) in 10% hydrogen chloride and methanol (30 mL) was stirred at room temperature for 3.5 hours. The solvent was distilled off under reduced pressure. Then, the obtained concentrated residue was adjusted to pH 8 by the addition of a saturated aqueous solution of sodium bicarbonate, and then water was distilled off under reduced pressure. The obtained concentrated residue was suspended by the addition of water (30 mL), and the resulting precipitate was collected by filtration, washed with water (1 mL), and then dried under reduced pressure to obtain the title compound (RE4) (787 mg, 90%) as a white powder.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionThen, the obtained concentrated residue was adjusted to pH 8 by the addition of a saturated aqueous solution of sodium bicarbonate
  3. distillationwater was distilled off under reduced pressure
  4. additionThe obtained concentrated residue was suspended by the addition of water (30 mL)
  5. filtrationthe resulting precipitate was collected by filtration
  6. washwashed with water (1 mL)
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-cc07f72526f94d5395e3681a9c4463b5
Source dataset
uspto-grants-2014_07
Patent number
US08778970B2

Reaction notes

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