Potassium Carbonate → HCID 15630145, compound

HRID 1437532Notes

Reaction equation

HRID 1437532 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].Br[CH:16]1[CH2:21][CH2:20][CH2:19][CH:18]=[CH:17]1>CN(C)C=O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH:21]1[CH2:20][CH2:19][CH2:18][CH:17]=[CH:16]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 119922-BromoanilineHCID 1370573-Bromocyclohexene

Product 1

HCID 15630145HCID 15630145, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 2-bromoaniline (2.0 g, 12 mmol) in N,N-dimethylformamide (15 mL) was added potassium carbonate (2.4 g, 18 mmol) and 3-bromocyclohexene (2.7 mL, 23 mmol). The mixture was heated at 75° C. for 16 hours. The reaction was allowed to cool before being diluted with ethyl acetate (50 mL) and toluene (15 mL). The solution was washed with brine, dried over magnesium sulfate, and concentrated. The residue was dried under high vacuum to yield 2.13 g (73%) of N-(2-bromophenyl)-N-cyclohex-2-en-1-ylamine. 1H NMR (DMSO-d6): δ 7.40 (d, 1H), 7.16 (t, 1H), 6.79 (d, 1H), 6.53 (t, 1H), 5.83-5.88 (m, 1H), 5.66-5.71 (m, 1H); 4.43 (d, 1H), 4.06 (m, 1H), 1.99 (m, 2H), 1.82 (m, 1H), 1.60 (m, 3H). MS m/z 252, 254 (M+1).

Workup

  1. temperatureto cool
  2. washThe solution was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-30c803e859c346519b902b98ca870bc9
Source dataset
uspto-grants-2009_11
Patent number
US07622494B2

Reaction notes

Loading…