Benzyl Bromide → HCID 15445561, compound

HRID 2082343Notes

Reaction equation

HRID 2082343 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[C:7]([NH2:9])=[O:8].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:10]([NH:9][C:7]([C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][NH:1]1)=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 6933831(S)-Piperidine-2-carboxamide

Product 1

HCID 15445561HCID 15445561, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 9.0 g (70.2 mmol) of (S)-piperidine-2-carboxamide (prepared by the method of Geotz Hardtmann, William Houlihan and Rudolf Giger, U.S. Pat. No. 4,760,065) in 100 mL of methylene chloride was added 24.0 g (140.4 mmol) of benzyl bromide and 7.2 g (70.2 mmol) of triethylamine. The mixture was stirred at room temperature for 24 h and washed with 1N aqueous sodium hydroxide. The organic layer was dried over anhydrous sodium sulfate and solvent was removed at reduced pressure. The residue was purified by silica gel chromatography using hexane:ethyl acetate (1:1) as eluent to give (S)-N-benzyl-piperidine-2-carboxamide (12.2 g, 80%), mp 103°-104° C., specific rotation=-90.7° (c=2.5, ethanol).

Workup

  1. customprepared by the method of Geotz Hardtmann, William Houlihan and Rudolf Giger, U.S
  2. washwashed with 1N aqueous sodium hydroxide
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate and solvent
  4. customwas removed at reduced pressure
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0b95b6b22b2b4702b07b16cfb38d8f68
Source dataset
uspto-grants-1993_02
Patent number
US05189046

Reaction notes

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