Hydrochloric Acid → 4-Cycloheptyloxy-benzylamine

HRID 911652Notes

Reaction equation

HRID 911652 reaction equation
[CH:1]1([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.Cl>C1COCC1>[CH:1]1([O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:13][NH2:14])=[CH:15][CH:16]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 576566254-(Cycloheptyloxy)benzonitrile

Product 1

HCID 576564054-Cycloheptyloxy-benzylamineYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4-cycloheptyloxy-benzonitrile (2 g, 9.29 mmol) in anhydrous THF (20 mL) and cool to 0° C. Add borane dimethylsulfide complex (2.8 mL, 27.9 mmol, 10-12 M solution), stir at 0° C. for 0.5 h and then heat at reflux for 1 h. Cool the mixture to 0° C., add methanol (5 mL) and stir for 15 min. Add 2M aqueous HCl (15 mL) and stir for 30 min at room temperature. Concentrate the mixture in vacuo and purify the residue by chromatography on silica gel (45 g RediSep column) eluting with a gradient of dichloromethane in chloroform/methanol/concentrated ammonium hydroxide (80:18:2) over 30 min (80 ml/min) to provide the title compound as a colorless oil (1.87 g, 97%). MS (APCI) m/z: 220 (M+H)+.

Workup

  1. temperatureheat
  2. temperatureat reflux for 1 h
  3. temperatureCool the mixture to 0° C.
  4. stirringstir for 15 min
  5. stirringstir for 30 min at room temperature
  6. concentrationConcentrate the mixture in vacuo
  7. custompurify the residue by chromatography on silica gel (45 g RediSep column)
  8. washeluting with a gradient of dichloromethane in chloroform/methanol/concentrated ammonium hydroxide (80:18:2) over 30 min (80 ml/min)

Sources & evidence

ORD record
ord-0e12d77ed012474ea82bbfecbed6c8f2
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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