Triethylamine → HCID 118207529, compound

HRID 1507234Notes

Reaction equation

HRID 1507234 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:18][CH:19]([CH2:23][CH2:24][Br:25])[C:20](Cl)=[O:21]>C(OCC)C>[Br:18][CH:19]([CH2:23][CH2:24][Br:25])[C:20]([NH:10][C@H:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:9])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 44131432,4-Dibromobutyryl chloride

Product 1

HCID 118207529HCID 118207529, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of (S)-1-(4-fluorophenyl)ethanamine (3.2 g, 23 mmol) in diethyl ether (50 mL) and triethylamine (9.6 mL, 69 mmol) at 0° C. was added 2,4-dibromobutanoyl chloride (7.3 g, 27.6 mmole) and the mixture was allowed to warm to rt and stirred for 12 h. A solid formed which was removed by filtration, washed with ethyl acetate, and then discarded. The combined filtrates were evaporated under reduced pressure and the residue was subjected to silica gel chromatography eluting with 20-30% ethyl acetate/petroleum ether yielding 4.5 g of 2,4-dibromo-N—((S)-1-(4-fluorophenyl)ethyl)butanamide as a brown solid. LCMS (method O) RT=0.99 min, m/z 366, 368, 370 (M+H+, M+H++2, M+H++4); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.25-1.44 (m, 3H) 2.27-2.46 (m, 2H) 3.46-3.58 (m, 2H) 4.55-4.66 (m, 1H) 4.81-5.00 (m, 1H) 7.03-7.24 (m, 2H) 7.30-7.45 (m, 2H) 8.89 (d, J=8.03 Hz, 1H).

Workup

  1. customA solid formed which
  2. customwas removed by filtration
  3. washwashed with ethyl acetate
  4. customThe combined filtrates were evaporated under reduced pressure
  5. washeluting with 20-30% ethyl acetate/petroleum ether yielding 4.5 g of 2,4-dibromo-N—((S)-1-(4-fluorophenyl)ethyl)butanamide as a brown solid

Sources & evidence

ORD record
ord-95fd07c453ed464fbc08008dff4c7dbe
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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