Boron tribromide → HCID 408376, compound

HRID 1529838Notes

Reaction equation

HRID 1529838 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([CH:18]=[CH:19][CH:20]=1)[CH2:10][NH:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]([CH:18]=[CH:19][CH:20]=1)[CH2:10][NH:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 4717165HCID 4717165, compound

Product 1

HCID 408376HCID 408376, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon atmosphere, BBr3 (9.1 mL of 1M solution in CH2Cl2 9.1 mmol) was slowly added at 0° C. to a solution of N-(3-methoxybenzyl)-cyclohexylamine in CH2Cl2 (40 mL). After stirring 3 h at room temperature, the reaction mixture was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate, filtered, and evaporated to provide 314 mg of cyclohexylamine 22 (50% yield) which was used without further purification. 1H NMR (300 MHz, acetone-d6) δ 1.12-1.31 (m, 5H), 1.59 (m, 1H), 1.73 (m, 2H), 1.92 (m, 2H), 2.53 (m, 1H), 3.77 (s, 2H), 6.70 (dd, J=1.9 and 8.9 Hz, 1H), 6.84 (d, J=7.4 Hz, 1H), 6.91 (s, 1H), 7.12 (t, J=7.8 Hz, 1H) ppm. N-(3-hydroxybenzyl)-piperidine 22b was obtained using the same procedure (25% overall yield). 1H NMR (300 MHz, acetone-d6) δ 1.50-2.30 (m, 6H), 2.80-3.50 (m, 4H), 4.18 (s, 2H), 6.94 (m, 1H), 7.24 (m, 2H), 7.34 (s, 1H), 8.91 (br s, 1H), 11.24 (br s, 1H) ppm.

Workup

  1. customthe reaction mixture was quenched with saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-da81c8571b5845b6bc88cdabc3a0dd0d
Source dataset
uspto-grants-2015_07
Patent number
US09090651B2

Reaction notes

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