Dichloromethane → HCID 69819398, compound

HRID 1006361Notes

Reaction equation

HRID 1006361 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.Cl.[CH:9]([CH:22]1[NH:27][C@@H:26]([CH2:28][OH:29])[CH2:25][N:24]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH3:38])[CH2:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.ClCCl.Cl[CH2:43][C:44](Cl)=[O:45]>O>[CH:9]([CH:22]1[N:27]2[C@@H:26]([CH2:28][O:29][CH2:43][C:44]2=[O:45])[CH2:25][N:24]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH3:38])[CH2:23]1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 69819609HCID 69819609, compound

Product 1

HCID 69819398HCID 69819398, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium carbonate (81.3 mg) was added to a mixture of [(2R)-6-benzhydryl-4-(2-methoxybenzyl)piperazin-2-yl]methanol dihydrochloride (48.0 mg) in a mixed solvent of dichloromethane and water. Chloroacetyl chloride was. added to the mixture below 5° C. and the whole was stirred for 1 hour. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated under reduced pressure. The resulting residue was dissolved into tert-butanol (4 ml) and potassium tert-butoxide (22.0 mg) was added to the mixture. The reaction mixture was poured into aqueous sodium hydrogen carbonate, and the whole was extracted with ethyl acetate. The extract was dried over magnesium sulfate, and evaporated under reduced pressure. The residue was purified by preparative TLC (15 PLC plate 20×20 cm, silica gel 60 F254, 1 mm, Merck) with a mixture of hexane and ethyl acetate as an eluent to give (9aR)-6-benzhydryl-8-(2-methoxybenzyl)hexahydropyrazino[2,1-c][1,4]oxazin-4-one (30 mg) as a colorless oil.

Workup

  1. additionadded to the mixture below 5° C.
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. dissolutionThe resulting residue was dissolved into tert-butanol (4 ml) and potassium tert-butoxide (22.0 mg)
  7. additionwas added to the mixture
  8. additionThe reaction mixture was poured into aqueous sodium hydrogen carbonate
  9. extractionthe whole was extracted with ethyl acetate
  10. dry with materialThe extract was dried over magnesium sulfate
  11. customevaporated under reduced pressure
  12. customThe residue was purified by preparative TLC (15 PLC plate 20×20 cm, silica gel 60 F254, 1 mm, Merck) with a mixture of hexane and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-a1a9039c735b40f690ea340094d24422
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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