Cyclopropylamine → HCID 118307040, compound

HRID 921221Notes

Reaction equation

HRID 921221 reaction equation
[CH2:1]([C:5]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:6]=1[CH:7]=O)[CH2:2][CH:3]=[CH2:4].[CH:14]1([NH2:17])[CH2:16][CH2:15]1.[BH4-].[Na+]>CO>[CH2:1]([C:5]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:6]=1[CH2:7][NH:17][CH:14]1[CH2:16][CH2:15]1)[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 118307060HCID 118307060, compound

Product 1

HCID 118307040HCID 118307040, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(but-3-en-1-yl)-4-fluorobenzaldehyde (50 mg, 0.281 mmol) and cyclopropanamine (16.02 mg, 0.281 mmol) in MeOH (2 mL) was stirred at rt for 30 min. Sodium borohydride (5.31 mg, 0.140 mmol) was added and stirred at rt for 1 h. It was then quenched with NH4Cl, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by biotage, eluting with 25% EtOAc/hexane to isolate N-(2-(but-3-en-1-yl)-4-fluorobenzyl)cyclopropanamine (20 mg, 0.091 mmol, 32.5% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.26 (dd, J=8.3, 6.1 Hz, 1H), 6.93-6.82 (m, 2H), 5.95-5.84 (m, 1H), 5.13-5.00 (m, 2H), 3.83 (s, 2H), 2.81-2.75 (m, 2H), 2.41-2.33 (m, 2H), 2.18 (tt, J=6.6, 3.5 Hz, 1H), 0.51-0.44 (m, 2H), 0.43-0.35 (m, 2H).

Workup

  1. stirringstirred at rt for 1 h
  2. customIt was then quenched with NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by biotage
  8. washeluting with 25% EtOAc/hexane

Sources & evidence

ORD record
ord-1085069e361d406e8e4848f5c35a5ad1
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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