Sodium Carbonate → HCID 22841641, compound

HRID 1460480Notes

Reaction equation

HRID 1460480 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][S:10](=[O:18])[C:9]2[CH:19]=[CH:20][CH:21]=[CH:22][C:8]1=2.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([CH2:29][CH2:30]Br)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([CH2:29][CH2:30][N:1]2[CH2:5][CH2:4][CH2:3][C@H:2]2[CH2:6][N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][S:10](=[O:18])[C:9]3[CH:19]=[CH:20][CH:21]=[CH:22][C:8]2=3)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 22841642HCID 22841642, compound

Product 1

HCID 22841641HCID 22841641, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (2S)-5,11-dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]thiazepine-10-oxide (see Preparation 19) (180 mg), 4-methoxyphenethyl bromide (140 mg) and sodium carbonate (70 mg) in acetonitrile (20 ml) was heated under reflux for 18 hours and evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water and the organic layer washed with water, dried over sodium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (5 g), performing a gradient elution initially using dichloromethane as eluant and changing to dichloromethane/methanol (98:2). Appropriate fractions were combined and evaporated under reduced pressure to give the title compound as a colourless oil, (50 mg, 19%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customevaporated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. washthe organic layer washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel (5 g)
  9. washa gradient elution initially using dichloromethane as eluant
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ba6d8d7619e34471a0924f86974b749c
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

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