Cyclopentylamine → HCID 43177392, compound

HRID 1853921Notes

Reaction equation

HRID 1853921 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[CH:11]1([NH2:16])[CH2:15][CH2:14][CH2:13][CH2:12]1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:16][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 7466p-BromoacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 43177392HCID 43177392, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(4-bromophenyl)ethanone (500 mg, 2.5 mmol) in ethanol (16 mL) was added cyclopentanamine (320 mg, 3.8 mmol) and the reaction mixture was heated at 50° C. for 18 h. The reaction mixture was cooled to 0° C. and sodium borohydride (140 mg, 3.8 mmol) was added and the reaction mixture was warmed to room temperature and stirred for 30 min. The reaction mixture was quenched with 2 M aqueous ammonium hydroxide and extracted with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford the desired product (600 mg, 90%) as a red oil: ESI MS m/z 269 [C13H18BrN+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. temperaturethe reaction mixture was warmed to room temperature
  3. customThe reaction mixture was quenched with 2 M aqueous ammonium hydroxide
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c312b93f4953427a91501f995998e415
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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