HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium hydride → 6,11-Dihydro-2,6-dimethyl-11-(3-dimethylamino-propyl)-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

HRID 1862976
Notes
Print preview

Reaction equation

HRID 1862976 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[N:10]([CH3:13])[C:9]3[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=3[NH:7][C:6]=2[N:18]=1.[H-].[Na+].[CH2:21]([N:23]([CH2:28]C)[CH2:24][CH2:25][CH2:26]Cl)C>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[N:10]([CH3:13])[C:9]3[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=3[N:7]([CH2:26][CH2:25][CH2:24][N:23]([CH3:28])[CH3:21])[C:6]=2[N:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669183-Chloropropyl(diethyl)amineHCID 203930286,11-Dihydro-2,6-dimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

Product 1

HCID 203930256,11-Dihydro-2,6-dimethyl-11-(3-dimethylamino-propyl)-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent
2×

Conditions

Temperature
120 °C

Procedure

A mixture consisting of 7.2 gm of 6,11-dihydro-2,6-dimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, 70 ml of dimethyl formamide and 1.9 gm of 50% sodium hydride in mineral oil was stirred at 30°-50° C. in a nitrogen atmosphere for 30 minutes. Then, a solution of 6.1 gm of 3-diethylamino-propyl chloride in 30 ml of dimethyl formamide was added dropwise, and the mixture was heated on an oil bath at 120° C. for 3 hours and then evaporated in vacuo. The residue was mixed with an aqueous potassium carbonate solution, and the mixture was extracted with ether. The ethereal phase was dried with sodium sulfate and evaporated, and the residue was recrystallized from petroleum ether (b.p. 100°-140° C.), yielding 76% of theory of the compound named in the heading, which had a melting point of 130°-131° C.

Workup

  1. customevaporated in vacuo
  2. additionThe residue was mixed with an aqueous potassium carbonate solution
  3. extractionthe mixture was extracted with ether
  4. dry with materialThe ethereal phase was dried with sodium sulfate
  5. customevaporated
  6. customthe residue was recrystallized from petroleum ether (b.p. 100°-140° C.)
  7. customyielding 76% of theory of the compound

Sources & evidence

ORD record
ord-fbe1de0b0dea4a48925d96834c981e64
Source dataset
uspto-grants-1979_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04167570

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes