Methanol → HCID 23317224, compound

HRID 1982103Notes

Reaction equation

HRID 1982103 reaction equation
Cl.[Cl:2][CH:3]1[CH2:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:6]=2[N:5]([CH3:22])[CH2:4]1.[Na].[CH3:24][OH:25]>>[ClH:2].[Cl:21][C:18]1[CH:19]=[CH:20][C:6]2[N:5]([CH3:22])[CH:3]([CH2:4][O:25][CH3:24])[CH2:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:7]=2[CH:17]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 12318099HCID 12318099, compound

Product 1

HCID 23317224HCID 23317224, compound

Procedure

500 mg of 3,8-dichloro-1-methyl-6-phenyl-1,2,3,4-tetrahydro-1,5-benzodiazocine hydrochloride were heated in a solution of 110 mg sodium in 70 ml methanol under reflux for 12 hours. After evaporation of the methanol in a vacuum the mass was further processed with water/chloroform and the chloroform solution was evaporated and concentrated in a vacuum. The residue was taken up in isopropanol and reacted with an ether solution of hydrogen chloride. There was obtained 7-chloro-1-methyl-2-methoxymethyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine hydrochloride which product also was identical with the product obtained directly by reaction of N-methyl-N-(2-hydroxy-3-benzoylaminopropyl)-4'-chloroaniline in phosphoroxychloride at 120° C. and subsequent reaction with sodium and methanol as disclosed in Examples 4 and 8 of application Ser. No. 355 986; m.p. 198°-210° C.

Workup

  1. temperatureunder reflux for 12 hours
  2. customAfter evaporation of the methanol in a vacuum the mass
  3. customthe chloroform solution was evaporated
  4. concentrationconcentrated in a vacuum
  5. customreacted with an ether solution of hydrogen chloride

Sources & evidence

ORD record
ord-9d1a9a0bfd9042909f99bce13c6023a3
Source dataset
uspto-grants-1986_06
Patent number
US04595531

Reaction notes

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