Thiomorpholine → 4-(3,5-Dimethoxybenzyl)thiomorpholine

HRID 1060479Notes

Reaction equation

HRID 1060479 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1)[CH2:12]Cl>C1COCC1>[CH3:18][O:17][C:15]1[CH:14]=[C:11]([CH2:12][N:1]2[CH2:6][CH2:5][S:4][CH2:3][CH2:2]2)[CH:10]=[C:9]([O:8][CH3:7])[CH:16]=1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 27583953,5-Dimethoxybenzyl chloride

Product 1

HCID 7560214-(3,5-Dimethoxybenzyl)thiomorpholineYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thiomorpholine (3.4 g) was added to a solution of 3,5-dimethoxybenzyl chloride (2 g) in THF (25 mL) and the mixture was stirred overnight at room temperature. The solid material was removed by filtration and the filtrate was evaporated. The residue was purified by column chromatography (silica gel; eluent: EtOAc/hexane 1/2) to yield 2 g of 3,5-dimethoxy-1-(thiomorpholino-methyl)benzene. ESMS: m/z 253 (M).

Workup

  1. customThe solid material was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography (silica gel; eluent: EtOAc/hexane 1/2)

Sources & evidence

ORD record
ord-7788b8a933b8460c8415281e474eb93e
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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