Hydrochloric Acid → HCID 19957051, compound

HRID 55004Notes

Reaction equation

HRID 55004 reaction equation
[ClH:1].Cl.C[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][N:14]([CH3:22])[C:13]([CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[N:12]2)=[CH:7][CH:6]=1.C([O-])(=O)/C=C/C([O-])=O.B(Br)(Br)Br.Cl>C(Cl)Cl>[ClH:1].[ClH:1].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][N:14]([CH3:22])[C:13]([CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=3)=[N:12]2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 5460307FumarateHCID 199571304,5-dihydro-1-(4-methoxyphenyl)-4-methyl-3-[2-(4-pyridyl)ethyl]-1H-2,4-benzodiazepine dihydrochloride

Product 1

HCID 19957051HCID 19957051, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4,5-dihydro-1-(4-methoxyphenyl)-4-methyl-3-[2-(4-pyridyl)ethyl]-1H-2,4-benzodiazepine dihydrochloride (3.81 g, 8.6 mmol, prepared from the fumarate of Example 398 by standard procedures) in CH2Cl2 (40 mL) in an ice-bath under N2 was added boron tribromide (17.2 mL, 1M in CH2Cl2). The mixture was stirred for 3 hours, 2N HCl was added and the mixture was stirred for 1/2 hour. The layers were separated, the aqueous layer was extracted with CH2Cl2 and the combined organic layers were washed with 2N HCl. The organic layer was treated with saturated Na2CO3 and the product which precipitates was collected by filtration to afford 3.06 g (83%) of 4,5-dihydro-1-(4-hydroxyphenyl)-4-methyl-3-[2-(4-pyridyl)ethyl]-1H-2,4-benzodiazepine dihydrochloride, m.p. 258°-259° C. after recrystallization from methanol/ether.

Workup

  1. stirringthe mixture was stirred for 1/2 hour
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washthe combined organic layers were washed with 2N HCl
  5. additionThe organic layer was treated with saturated Na2CO3
  6. customthe product which precipitates
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-a4b8f0eb5792475cbef6c6c77c06bd3c
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Reaction notes

Loading…