HCID 20393036, compound → HCID 20393027, compound

HRID 1862981Notes

Reaction equation

HRID 1862981 reaction equation
[CH2:1]([N:3]([CH2:11][CH2:12][CH2:13][N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]([CH3:25])[C:17](=[O:26])[C:16]2[C:27]([CH3:32])=[CH:28][C:29]([CH3:31])=[N:30][C:15]1=2)CC1C=CC=CC=1)[CH3:2]>CO.[Pd]>[CH2:1]([NH:3][CH2:11][CH2:12][CH2:13][N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]([CH3:25])[C:17](=[O:26])[C:16]2[C:27]([CH3:32])=[CH:28][C:29]([CH3:31])=[N:30][C:15]1=2)[CH3:2]

Participants

4

Reactant 1

HCID 20393036HCID 20393036, compound

Product 1

HCID 20393027HCID 20393027, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

14 gm of the end product of step (a) were hydrogenated in 400 ml of methanol in the presence of 5 gm of 10% palladium-on-charcoal at 50° C. and 50 atmospheres. After separating the catalyst, the reaction mixture was evaporated in vacuo, and the residue was purified on a silica gel column. Then, the product was recrystallized from petroleum ether (b.p. 100°-140° C.), yielding 42% of theory of 11-(3-ethylamino-propyl)-6,11-dihydro-2,4,6-trimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one which had a m.p. of 101°-103° C.

Workup

  1. customAfter separating the catalyst
  2. customthe reaction mixture was evaporated in vacuo
  3. customthe residue was purified on a silica gel column
  4. customThen, the product was recrystallized from petroleum ether (b.p. 100°-140° C.)

Sources & evidence

ORD record
ord-cc35fa4554de4f40b993c0a3f74d58af
Source dataset
uspto-grants-1979_09
Patent number
US04167570

Reaction notes

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