Ethyl Acetate → HCID 22373374, compound

HRID 2392574Notes

Reaction equation

HRID 2392574 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]4[C:22](=[O:23])[C:21]5=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]5[C:19]4=[O:28])[CH2:12][CH2:11]3)=[CH:8][S:7][C:6]=2[CH:29]=1.[BH4-].[Na+].CCCCCCC.CCOC(C)=O>CCO.ClCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]4[CH:22]([OH:23])[C:21]5[C:20](=[CH:27][CH:26]=[CH:25][CH:24]=5)[C:19]4=[O:28])[CH2:12][CH2:11]3)=[CH:8][S:7][C:6]=2[CH:29]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 4311764Sodium borohydrideHCID 18980221HCID 18980221, compound

Product 1

HCID 22373374HCID 22373374, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 24526ChlorineSolvent

Procedure

To a stirred suspension of N-[2-[4-(6-fluorobenzo[b]thien-3-yl)-1-piperazinyl]-ethyl]phthalimide (2.7 g, 6.6 mmol) in a mixture of 200 ml absolute EtOH and 50 ml CH2 Cl2 under N2 was added Sodium Borohydride (0.56 g, 14.8 mmol) in one portion. The mixture was stirred at room temperature for 15 minutes, during which time the solids dissolved. At the end of 15 minutes, TLC [silica, 1:1 heptane:EtOAc] showed no starting material remained and a major, lower Rf spot had appeared.

Workup

  1. dissolutiondissolved

Sources & evidence

ORD record
ord-e9d7d9b663384e00bc83b3227d737a5a
Source dataset
uspto-grants-1998_09
Patent number
US05801176

Reaction notes

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