3-Bromoaniline → N-(3-bromophenyl)cyclohexanecarboxamide

HRID 716756Notes

Reaction equation

HRID 716756 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14]>CN(C1C=CN=CC=1)C.C1COCC1>[Br:10][C:11]1[CH:12]=[C:13]([NH:14][C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:8])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 115623-BromoanilineHCID 75938Cyclohexanecarbonyl chloride

Product 1

HCID 849114N-(3-bromophenyl)cyclohexanecarboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Cyclohexanecarbonyl chloride (0.74 g, 6.97 mmol) was added to a mixture of 3-bromoaniline (1.0 g, 5.8 mmol), TEA (1.07 mL, 7.55 mmol) and DMAP (cat.) in THF with stirring at 0° C. over 10 min. Stirring was continued for another 30 min and quenched with saturated NaHCO3. The product was extracted with ethyl acetate. Combined organic layers were concentrated under reduced pressure to give a residue which was triturated with pentane to give N-(3-bromophenyl)cyclohexanecarboxamide as an off-white solid. Yield (1.3 g, 79%); 1H NMR (400 MHz, DMSO-d6) δ 9.96 (s, 1H), 7.97 (s, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.26-7.18 (m, 2H), 2.33-2.26 (m, 1H), 1.76 (t, J=14.0 Hz, 4H), 1.65 (d, J=10.4 Hz, 1H), 1.43-1.34 (m, 2H), 1.30-1.12 (m, 3H).

Workup

  1. stirringStirring
  2. waitwas continued for another 30 min
  3. customquenched with saturated NaHCO3
  4. extractionThe product was extracted with ethyl acetate
  5. concentrationCombined organic layers were concentrated under reduced pressure
  6. customto give a residue which
  7. customwas triturated with pentane

Sources & evidence

ORD record
ord-09e832bfba71447bbec901025cb6643e
Source dataset
uspto-grants-2015_11
Patent number
US09193669B2

Reaction notes

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