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

HRID 516807Notes

Reaction equation

HRID 516807 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-a24f56070fce4ebc975a0c9acf2aec59
Source dataset
uspto-grants-2015_08
Patent number
US09115064B2

Reaction notes

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