Benzyl Chloride → (cis)-2-Benzyl-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one

HRID 1871402Notes

Reaction equation

HRID 1871402 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[C@H:22]3[C@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)[C:16](=[O:23])[NH:15][N:14]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C=O>[CH2:24]([N:15]1[N:14]=[C:13]([C:7]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:5]([O:4][CH3:3])[CH:6]=2)[C@H:22]2[C@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]2)[C:16]1=[O:23])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 10913208(cis)-4-(3,4-Dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one

Product 1

HCID 70001660(cis)-2-Benzyl-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6 mmol of a 60% suspension of sodium hydride in mineral oil was added to a suspension of 5 mmol of compound 1 in about 40 ml of dimethylformamide, under a flow of nitrogen at room temperature. After stirring this mixture for 30 minutes, 7 mmol of benzylchloride was added and the resulting mixture was stirred for another 4 hours, after which the solvent was evaporated. The residue was partitioned between ethyl acetate and water, the organic layer was dried over magnesium sulfate and evaporated. The residue was crystallized from methanol. M.p. 117°-118° C.

Workup

  1. stirringthe resulting mixture was stirred for another 4 hours
  2. customafter which the solvent was evaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-88fcb6379b564b49991aee24f693ab72
Source dataset
uspto-grants-2000_08
Patent number
US06103718

Reaction notes

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