Propanal → [1-(4-Bromophenyl)-cyclopropyl]dipropylamine

HRID 1935916Notes

Reaction equation

HRID 1935916 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH2:11])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:12]1[CH2:16]OC[CH2:13]1.[CH:17](=O)[CH2:18][CH3:19].[BH3-]C#N.[Na+]>CC#N.CC(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([N:11]([CH2:13][CH2:12][CH3:16])[CH2:17][CH2:18][CH3:19])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 527PropanalHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 187101951-(4-Bromophenyl)cyclopropanamine2×

Product 1

HCID 22568796[1-(4-Bromophenyl)-cyclopropyl]dipropylamine

Reagents, catalysts & solvents 1

HCID 22391770Acetonitrile aceticacidSolvent

Procedure

To a solution of 1-(4-bromophenyl)-cyclopropylamine (Intermediate 116) in CH3CN/HOAc (5 mL, 9:1, v/v) and THF 3 mL at 0° C. was added propionaldehyde (277.0 mg, 4.95 mmols) and NaCNBH3 (153.0 mg, 2.47 mmols). The reaction was warmed to room temperature and after 5hours quenched with H2O. The pH of the solution was adjusted to 8-9 using aqueous NaOH and extracted with EtOAc. The combined extracts were washed with H2O and saturated aqueous NaCl, dried (MgSO4) and concentrated under reduced pressure. The title compound, 190.0 mg (56%), was isolated by column chromatography (2-5% EtOAc-hexanes).

Workup

  1. customquenched with H2O
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O and saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ece68a1d20041ea9b6775c2b959557b
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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