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

HRID 841462Notes

Reaction equation

HRID 841462 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 5 hours 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-5df1134c6e6743ac87d74191ee99b725
Source dataset
uspto-grants-2002_04
Patent number
US06369225B1

Reaction notes

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