Dimethylamine → HCID 20542086, compound

HRID 2286170Notes

Reaction equation

HRID 2286170 reaction equation
[CH3:1][NH:2][CH3:3].[C:4]([C:7]1[CH:8]=[CH:9][C:10]2[N:16]([CH2:17][CH3:18])[C:15](=[O:19])[CH2:14][N:13]=[C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:11]=2[CH:27]=1)(=O)[CH3:5].C([BH3-])#N.[Na+]>CO.Cl>[CH3:1][N:2]([CH3:3])[CH:4]([C:7]1[CH:8]=[CH:9][C:10]2[N:16]([CH2:17][CH3:18])[C:15](=[O:19])[CH2:14][NH:13][CH:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:11]=2[CH:27]=1)[CH3:5]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 5003444Sodium cyanoborohydride2×HCID 20542077HCID 20542077, compound

Product 1

HCID 20542086HCID 20542086, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution, stirred at room temperature, of 9.1 ml of dimethylamine in 140 ml of methanol and 0.1 ml of 5 N methanolic hydrochloric acid are added 7.0 g (21.7 mmol) of 7-acetyl-1-ethyl-5-(o-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one, followed by 0.24 g of sodium cyanoborohydride. The mixture is stirred at room temperature for 14 days, with 924 mg of sodium cyanoborohydride being added after 2 days and after 7 days. The solvent is removed in vacuo and the residue is adjusted to pH 10 with 10 N sodium hydroxide and then taken up in chloroform. The organic phase is washed with water, dried and evaporated. The residue is chromatographed on 200 g of silica gel using chloroform as the elution agent and there is obtained 7-[1-(dimethylamino)ethyl]-1-ethyl-5-(o-fluorophenyl)-1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one as an oil.

Workup

  1. additionadded after 2 days and after 7 days
  2. customThe solvent is removed in vacuo
  3. washThe organic phase is washed with water
  4. customdried
  5. customevaporated
  6. customThe residue is chromatographed on 200 g of silica gel

Sources & evidence

ORD record
ord-60893511c5284b65b83523a785bb6eab
Source dataset
uspto-grants-1982_04
Patent number
US04327026

Reaction notes

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