5-(3,4-Dimethoxy-phenyl)-thiomorpholine-3-carboxylic acid (4-chloro-3-methoxy-phenyl)-amide → (4-Chloro-3-methoxy-phenyl)-[5-(3,4-dimethoxy-phenyl)-thiomorpholin-3-ylmethyl]-amine

HRID 1294612Notes

Reaction equation

HRID 1294612 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[CH2:16][S:15][CH2:14][CH:13]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=3)[NH:12]2)=O)=[CH:4][C:3]=1[O:27][CH3:28]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH:11]2[CH2:16][S:15][CH2:14][CH:13]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=3)[NH:12]2)=[CH:4][C:3]=1[O:27][CH3:28]

Participants

3

Reactant 1

HCID 865972335-(3,4-Dimethoxy-phenyl)-thiomorpholine-3-carboxylic acid (4-chloro-3-methoxy-phenyl)-amide

Product 1

HCID 22021964(4-Chloro-3-methoxy-phenyl)-[5-(3,4-dimethoxy-phenyl)-thiomorpholin-3-ylmethyl]-amineYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To an ice chilled suspension containing 5-(3,4-dimethoxy-phenyl)-thiomorpholine-3-carboxylic acid (4-chloro-3-methoxy-phenyl)-amide n(71 mg, 0.17 mmol, 1.0 equivalents) in toluene (1.5 ml) was added a 0.5M solution of alane (1.6 ml, 0.8 mmol, 4.8 equivalents). The reaction was stirred at room temperature for 2 hours. The reaction was quenched with 1N NaOH and extracted 3 times with dichloromethane. The dichloromethane extracts were dried with MgSO4, filtered and concentrated to yield (4-chloro-3-methoxy-phenyl)-[5-(3,4-dimethoxy-phenyl)-thiomorpholin-3-ylmethyl]-amine as an oil (65 mg, 95% yield). H1 NMR (400 MHz, CDCl3): 7.11 (1H, d), 6.93 (2H, m), 6.80 (1H, m), 6.19 (m, 2H), 3.86 (10H, m), 3.19 (3H, m), 2.80 (2H, m), 2.50 (2H, m). (LC-MS): Calculated for C20H25ClN2O3S 409.13. Found 409.23.

Workup

  1. customThe reaction was quenched with 1N NaOH
  2. extractionextracted 3 times with dichloromethane
  3. dry with materialThe dichloromethane extracts were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-09c40f11d4b94a71b3fb78ae8901daa9
Source dataset
uspto-grants-2007_07
Patent number
US07241765B2

Reaction notes

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