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

HRID 1069967Notes

Reaction equation

HRID 1069967 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 Shours 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. customafter Shours quenched 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-351261f1d23742c48ebce4f4d44b8d26
Source dataset
uspto-grants-2001_06
Patent number
US06252090B1

Reaction notes

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