2-Methylbenzonitrile → Cyclopropyl(2-methylphenyl)methanamine

HRID 874731Notes

Reaction equation

HRID 874731 reaction equation
Br[CH:2]1[CH2:4][CH2:3]1.[CH3:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[C:8]#[N:9].[BH4-].[Na+]>>[CH:2]1([CH:8]([C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[CH3:5])[NH2:9])[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 107212-MethylbenzonitrileHCID 78037BromocyclopropaneHCID 4311764Sodium borohydride

Product 1

HCID 3975922Cyclopropyl(2-methylphenyl)methanamineYield 108.5%

Procedure

The title compound was synthesized according to method G, utilizing Mg powder (240 mg, 10 mmol), bromocyclopropane (1.21 g, 10 mmol), 2-methylbenzonitrile (468 mg, 4 mmol), and NaBH4 (380 mg, 10 mmol). The reaction mixture was concentrated and purified by Biotage SiO2 column (gradient: MeOH/DCM 0-20%) to give cyclopropyl(o-tolyl)methanamine as a yellow oil (0.70 g, 87%) which solidified upon standing. 1H NMR (400 MHz, CD3OD) δ ppm 8.49 (d, J=7.6 Hz, 1H), 7.27-7.22 (m, 1H), 7.20-7.17 (m, 2H), 3.75 (d, J=8.4 Hz, 1H), 2.35 (s, 3H), 1.37-1.27 (m, 1H), 0.71-0.63 (m, 1H), 0.53-0.46 (m, 1H), 0.38-0.31 (m, 1H), 0.29-0.33 (m, 1H); MS ESI 145.0 [M+H]+, calcd for [C11H15N—NH2+H]+ 145.1.

Workup

  1. customThe title compound was synthesized
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by Biotage SiO2 column (gradient: MeOH/DCM 0-20%)

Sources & evidence

ORD record
ord-4615bdafd19143e7ab9b0a28eaedae40
Source dataset
uspto-grants-2015_03
Patent number
US08980934B2

Reaction notes

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