Sodium borohydride → HCID 55036, compound

HRID 2417617Notes

Reaction equation

HRID 2417617 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:27])[CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[C:20](=[O:26])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:15][CH2:14]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[BH4-].[Na+]>CO.C(Cl)(Cl)Cl>[OH:27][CH:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[C:20](=[O:26])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 13298561HCID 13298561, compound

Product 1

HCID 55036HCID 55036, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 2-[4-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-1-piperazinyl]-2,4,6-cycloheptatrien-1-one (1.33 g, described above) in methanol (20 ml) and chloroform (5 ml), sodium borohydride (0.31 g) was added portionwise over a period of one hr. The solvent was then removed under vacuum. The residue was taken up in chloroform, washed with water, ammonium chloride solution followed by water, dried and evaporated to give the title compound (1.33 g): mp 122°-124° C.; ir(CHCl3) 3420, 1565, 1260 and 1140 cm-1 ; uv max(MeOH) 352 (ε=10040), 256 (ε=15660) and 227 nm (ε=20250); nmr(CDCl3) δ2.6 (m, 6H), 3.3 (m, 4H), 3.85 (s, 6H), 4.7 (m,1H) and 6.8 (m,6H); and Anal. Calcd for C21H26N2O4 : C, 68.08% H, 7.08% N, 7.56% and Found: C, 67.78% H, 7.06% N, 7.36%.

Workup

  1. customThe solvent was then removed under vacuum
  2. washwashed with water, ammonium chloride solution
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-c7fb2629372847f18e853da843972340
Source dataset
uspto-grants-1984_09
Patent number
US04469695

Reaction notes

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