Hydrochloric Acid → HCID 57040738, compound
Reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C@H:8]2[CH2:17][N:12]3[CH2:13][CH2:14][NH:15][CH2:16][C@@H:11]3[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.F[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C@H:8]2[CH2:17][N:12]3[CH2:13][CH2:14][N:15]([C:21]4[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=4)[CH2:16][C@@H:11]3[CH2:10][CH2:9]2)=[CH:18][CH:19]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
A mixture of 0.500 g (1.89 mmol) of (7R,9aS)-7-(4-fluorophenoxy)methyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (Preparation 8), 0.400 g (2.84 mmol) of 4-fluoronitrobenzene and 0.401 g (3.78 mmol) of sodium carbonate in 15 mL of DMSO was heated at 95° C. for 16 h. The mixture was cooled to room temperature, acidified with 1M HCl, washed with ethyl ether (3×), basified with conc. ammonium hydroxide and extracted with ethyl acetate (3×). The combined organic layers were washed with water and brine, dried (magnesium sulfate), filtered and evaporated to give 0.614 g of (7R,9aS)-7-(4-fluorophenoxy)methyl-2-(4-nitrophenyl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine.
Workup
- temperatureThe mixture was cooled to room temperature
- washwashed with ethyl ether (3×)
- extractionextracted with ethyl acetate (3×)
- washThe combined organic layers were washed with water and brine
- dry with materialdried (magnesium sulfate)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-d9451f317a474454b235cf679e31bd09
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05852031
Reaction notes
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