Morpholine → 4-[2-(Morpholine-4-sulfonyl)-ethyl]-phenylamine

HRID 1989040Notes

Reaction equation

HRID 1989040 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][S:12](Cl)(=[O:14])=[O:13])=[CH:6][CH:5]=1)([O-])=O.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>C1COCC1>[N:16]1([S:12]([CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)(=[O:14])=[O:13])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 27611752-(4-nitrophenyl)ethanesulfonyl Chloride

Product 1

HCID 589945154-[2-(Morpholine-4-sulfonyl)-ethyl]-phenylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Nitro-phenyl)-ethanesulfonyl chloride (from Example 33 (A), 300 mg) was suspended in 5 mL of THF. To the stirring solution was added morpholine (1 mL) dropwise at r.t. After 5 hours the solvent was evaporated. The nitro product was purified by flash chromatography (CH2Cl2/CH3OH 10:1 v/v) and was converted to the title compound under normal hydrogenation conditions. The title compound was obtained as a yellow solid (167 mg, 52%). 1H NMR (400 MHz, CD3OD) δ (ppm): 7.01 (d, J=8.4 Hz, 2H), 6.65 (d, J=8.4 Hz, 2H), 3.72 (t, J=4.7 Hz, 4H), 3.23 (t, J=4.7 Hz, 4H), 3.11 (m, 2H), 2.98 (m, 2H).

Workup

  1. customAfter 5 hours the solvent was evaporated
  2. customThe nitro product was purified by flash chromatography (CH2Cl2/CH3OH 10:1 v/v)

Sources & evidence

ORD record
ord-66bc128970314c0387696ac3d22604f7
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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