2-Chloro-N,N-dimethylethylamine → 2,9-dihydro-2-[2-(dimethylamino)ethyl]-9-(piperidinoacetyl)-3H-pyrido[3,2-c]-s-triazolo[4,3-a]-[1,5]benzodiazepin-3-one

HRID 1658793Notes

Reaction equation

HRID 1658793 reaction equation
[N:1]1([CH2:7][C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]3[C:21](=[O:24])[NH:22][N:23]=[C:13]3[C:12]3[CH:25]=[CH:26][CH:27]=[N:28][C:11]2=3)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:32][CH2:33][N:34]([CH3:36])[CH3:35]>CN(C)C=O.C1(C)C(C)=CC=CC=1>[CH3:35][N:34]([CH3:36])[CH2:33][CH2:32][N:22]1[C:21](=[O:24])[N:14]2[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:10]([C:8](=[O:9])[CH2:7][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:11]3[N:28]=[CH:27][CH:26]=[CH:25][C:12]=3[C:13]2=[N:23]1

Participants

6

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 21525547HCID 21525547, compound

Product 1

HCID 215255642,9-dihydro-2-[2-(dimethylamino)ethyl]-9-(piperidinoacetyl)-3H-pyrido[3,2-c]-s-triazolo[4,3-a]-[1,5]benzodiazepin-3-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7237O-XyleneSolvent

Procedure

In the manner given in Example 25, to 2,9-dihydro-9-(piperidinoacetyl)-3 H-pyrido[3,2-c]-s-triazolo-[4,3-a][1,5]benzodiazepin-3-one in dimethylformamide is added a solution of sodium hydride in mineral oil. The mixture is allowed to react at about 95° C. for 40 minutes and after cooling (2-chloroethyl)dimethylamine in xylene is added. The mixture is kept at 95°-100° C. for a period of 22 hours, evaporated and worked up as in example 25 to give 2,9-dihydro-2-[2-(dimethylamino)ethyl]-9-(piperidinoacetyl)-3H-pyrido[3,2-c]-s-triazolo[4,3-a]-[1,5]benzodiazepin-3-one.

Workup

  1. customto react at about 95° C. for 40 minutes
  2. additionis added
  3. customevaporated

Sources & evidence

ORD record
ord-962818d3a02d460c82acd03477c89429
Source dataset
uspto-grants-1976_06
Patent number
US03966736

Reaction notes

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