Acetic Acid → [1-(4-Bromophenyl)-cyclopropyl]dipropylamine

HRID 844759Notes

Reaction equation

HRID 844759 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.[CH3:12][C:13](O)=O.[CH:16](=O)[CH2:17][CH3:18].[BH3-][C:21]#N.[Na+]>CC#N.C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([N:11]([CH2:21][CH2:13][CH3:12])[CH2:16][CH2:17][CH3:18])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 187101951-(4-Bromophenyl)cyclopropanamine2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

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 i277.0 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-56945f8f3c314d598d4089313b48616a
Source dataset
uspto-grants-2002_04
Patent number
US06380256B1

Reaction notes

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