Water → HCID 22506219, compound

HRID 1814416Notes

Reaction equation

HRID 1814416 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.[Br:11][CH2:12][CH2:13][CH2:14][NH2:15].C(N(CC)CC)C.O>CN(C=O)C>[C:1]1([NH:7][C:8]([NH:15][CH2:14][CH2:13][CH2:12][Br:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 787013-Bromopropylamine hydrobromide

Product 1

HCID 22506219HCID 22506219, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Phenyl isocyanate (1.4 ml, 13 mmol) was added to a solution of 3-bromopropylamine hydrobromide (2.5 g, 11 mmol) and triethylamine (1.7 ml, 12 mmol) in DMF (50 ml) at 0° C., and the mixture was stirred at 0° C. for 1.5 h. After adding water, the mixture was extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate, and filtered. The filtrate was concentrated under vacuum to dryness, and the residue was chromatographed on silica gel (eluting with 2.5% ethyl acetate/hexane to 50% ethyl acetate/hexane) to afford N-phenylcarbamoyl-3-bromopropylamine (2.7 g, 96%); MS(FD) m/e 256 M+; 1H NMR (400 MHz, CDCl3) δ 7.35-7.26 (m, 4H), 7.11 (m, 1H), 6.45 (br, 2H), 3.46 (t, J=6.3 Hz, 2H), 3.41 (t, J=6.6 Hz, 2H), 2.10 (m, 2H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum to dryness
  6. customthe residue was chromatographed on silica gel (eluting with 2.5% ethyl acetate/hexane to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-99c494939baa4bd7bc35c489599ccbf3
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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