Cyclopropylamine → 2-(4-Bromo-phenyl)-N-cyclopropyl-propionamide

HRID 409718Notes

Reaction equation

HRID 409718 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.CC[N:15]([CH:19]([CH3:21])[CH3:20])C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1(N)CC1>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:12])[C:9]([NH:15][CH:19]2[CH2:21][CH2:20]2)=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 5214412-(4-Bromophenyl)propanoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 843563282-(4-Bromo-phenyl)-N-cyclopropyl-propionamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 18.0 g (79.0 mmol) 2-(4-bromo-phenyl)-propionic acid (Bioorg. Med. Chem. Lett. 2010, 20, 887) and 68.4 mL (393 mmol) DIPEA in 90 mL DMF, 50.5 g (157 mmol) TBTU are added. The mixture is stirred for 15 min at 0° C. After that time, 16.3 mL (236 mmol) cyclopropylamine are added and the mixture is stirred for 16 h at rt. After that time, iced water is added and the mixture is extracted with EtOAc. The organic layer is washed with brine and dried over sodium sulphate. The solvent is evaporated and the residue is purified by column chromatography (silica gel; hexane/EtOAc 7:3) to yield the desired product.

Workup

  1. additionare added
  2. stirringthe mixture is stirred for 16 h at rt
  3. extractionthe mixture is extracted with EtOAc
  4. washThe organic layer is washed with brine
  5. dry with materialdried over sodium sulphate
  6. customThe solvent is evaporated
  7. customthe residue is purified by column chromatography (silica gel; hexane/EtOAc 7:3)

Sources & evidence

ORD record
ord-40014c6d3dcb40f78be0041792940b3b
Source dataset
uspto-grants-2014_06
Patent number
US08759528B2

Reaction notes

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