HCID 13457113, compound → HCID 13457123, compound

HRID 462422Notes

Reaction equation

HRID 462422 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=3)=[O:18])[CH2:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[CH2:8][OH:9].[H][H]>O1CCCC1.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=3)=[O:18])[CH2:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[CH2:8][OH:9]

Participants

5

Reactant 2

HCID 13457113HCID 13457113, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13457123HCID 13457123, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[4-[3-chloro-4-(hydroxymethyl)phenyl]-1-piperazinyl]-1(3-nitrophenyl)ethanone (1.5 g, 3.8 m mole) in 100 ml of tetrahydrofuran was catalytically reduced at 25° over 0.5 g of Raney-Nickel with an average of three atmospheres of hydrogen. When the theoretical amount of hydrogen had been absorbed, the mixture was filtered and the filtrate was evaporated at reduced pressure to give a yellow solid which was recrystallized from acetonitrile to afford 0.95 g (69%), mp 174.5°-180° (Table 1). Prepared in the like manner were Cpd. 37 (Table 2) and 26 (Table 1).

Workup

  1. customWhen the theoretical amount of hydrogen had been absorbed
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated at reduced pressure
  4. customto give a yellow solid which
  5. customwas recrystallized from acetonitrile
  6. customto afford 0.95 g (69%), mp 174.5°-180° (Table 1)
  7. customPrepared in the like manner

Sources & evidence

ORD record
ord-02cc53a9aa494d319a26915cea6f63ad
Source dataset
uspto-grants-1985_05
Patent number
US04515793

Reaction notes

Loading…