Diisopropylethylamine → 4-Bromo-N-(2-morpholin-4-ylethyl)thiophene-2-carboxamide

HRID 1189720Notes

Reaction equation

HRID 1189720 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7](Cl)=[O:8])[S:5][CH:6]=1.CCN(C(C)C)C(C)C.[NH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([NH:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[O:8])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4082852-MorpholinoethylamineHCID 27954834-Bromo-2-Thiophenecarbonyl Chloride

Product 1

HCID 230637244-Bromo-N-(2-morpholin-4-ylethyl)thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-thiophenecarbonyl chloride (1.0 g, 4.4 mmol) in DCM (10 ml) cooled to 0° C. was added DIPEA (0.85 ml, 4.8 mml) and 4-(2-aminoethyl)morpholine (0.6 ml, 4.6 mmol) dropwise. Stirring was continued until complete consumption of the starting material was observed by LC-MS. The reaction was quenched by the addition of water, which was washed with further portions of 2N HCl, dried over sodium sulfate, filtered and concentrated in vacuo to yield the desired compound without need for further purification (1.6 g, 98%). δH (500 MHz, CHLOROFORM-d) 7.38 (1H, d, 1.3 Hz), 7.37 (1H, d, 1.1 Hz), 3.72-3.80 (4H, m), 3.53 (2H, q, 5.6 Hz), 2.59 (2H, t, 6.0 Hz), 2.48-2.54 (4H, m), TR=0.8 min.

Workup

  1. customwas continued until complete consumption of the starting material
  2. customThe reaction was quenched by the addition of water, which
  3. washwas washed with further portions of 2N HCl
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f73d1a912a0c4c8a9ebfb01cca084275
Source dataset
uspto-grants-2014_03
Patent number
US08674132B2

Reaction notes

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