Tetrahydrofuran → [4-(Cyclopentyloxy)phenyl]methanamine

HRID 911641Notes

Reaction equation

HRID 911641 reaction equation
C1COCC1.[CH:6]1([O:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1>Cl>[CH:6]1([O:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:16][NH2:17])=[CH:18][CH:19]=2)[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 24690142HCID 24690142, compound

Product 1

HCID 16786769[4-(Cyclopentyloxy)phenyl]methanamineYield 73%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Add a solution of 1M BH3-THF complex in THF (4.8 mL, 4.8 mmol) to neat 4-cyclopentyloxy-benzonitrile (300 mg, 1.6 mmol) and stir the mixture for 3 h at room temperature and then for 3 h at reflux. Cool to room temperature, pour the reaction into 2N aqueous HCl (10 mL) and stir the mixture for 1 h at room temperature then concentrate in vacuo. Dissolve the crude mixture in methanol and filter through SCX column eluting with methanol followed by 3M ammonia in methanol to obtain the title compound (223 mg, 73%).

Workup

  1. temperaturefor 3 h at reflux
  2. temperatureCool to room temperature
  3. additionpour
  4. stirringstir the mixture for 1 h at room temperature
  5. concentrationthen concentrate in vacuo
  6. dissolutionDissolve the crude mixture in methanol
  7. filtrationfilter through SCX column
  8. washeluting with methanol

Sources & evidence

ORD record
ord-63b8423b98044a8c8ae61f6e9b1f37ac
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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