Water → HCID 86282690, compound

HRID 1424384Notes

Reaction equation

HRID 1424384 reaction equation
[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][C:6]2[CH2:7][C:8](=[O:22])[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:10](=O)[CH2:11][C:5]=2[CH:4]=1.[Cl-].[NH4+].O.ClCCl>C1COCC1>[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][C:6]2[CH2:7][C:8](=[O:22])[N:9]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[CH:10]=[CH:11][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 90465074HCID 90465074, compound

Product 1

HCID 86282690HCID 86282690, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g of LiBH(Et)3 (1.12 mmol, 1.33 eq, 1M solution in THF) is added to a solution of 7,8-dimethoxy-3-(4-methoxybenzyl)-1H-3-benzazepine-2,4(3H,5H)-dione (300 mg, 0.84 mmol) in THF (4.5 mL) at −78° C. The reaction mixture is held at that temperature for 1 hour 30 minutes with stirring and then hydrolysed with saturated aqueous ammonium chloride solution (4 mL). After a slow return to ambient temperature, 2 mL of water and 5 mL of dichloromethane are introduced, the aqueous phase is extracted with 10 mL of dichloromethane, and the organic phase is dried. The crude product obtained is purified by flash chromatography on a silica column (dichloromethane/methanol 98/2) to obtain the title product.

Workup

  1. extractionthe aqueous phase is extracted with 10 mL of dichloromethane
  2. customthe organic phase is dried
  3. customThe crude product obtained
  4. customis purified by flash chromatography on a silica column (dichloromethane/methanol 98/2)

Sources & evidence

ORD record
ord-8f8d30d4b72b4653a4ddf76674ac31c3
Source dataset
uspto-grants-2015_01
Patent number
US08927708B2

Reaction notes

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