Pyridine → HCID 86753322, compound

HRID 356187Notes

Reaction equation

HRID 356187 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][CH2:17][CH2:18][CH2:19][C@H:12]2[NH:11][C:10]2[CH:20]=[CH:21][CH:22]=[CH:23][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1(=[O:38])[N:28]([CH2:29][C:30](Cl)=[O:31])[C:27](=[O:33])[C:26]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:25]12.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>ClCCCl>[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][CH2:17][CH2:18][CH2:19][C@H:12]2[N:11]([C:30](=[O:31])[CH2:29][N:28]2[C:27](=[O:33])[C:26]3=[CH:34][CH:35]=[CH:36][CH:37]=[C:25]3[C:24]2=[O:38])[C:10]2[CH:20]=[CH:21][CH:22]=[CH:23][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 516892Sodium BicarbonateHCID 70111114(4aR*,11aS*)-10-benzyl-1,2,3,4,4a,5,10,11a-octahydro-11H-dibenzo[b,e][1,4]-diazepin-11-one

Product 1

HCID 86753322HCID 86753322, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (4aR*,11aS*)-10-benzyl-1,2,3,4,4a,5,10,11a-octahydro-11H-dibenzo[b,e][1,4]-diazepin-11-one (200 mg, 0.65 mmol) in 1,2-dichloroethane (2 mL) was added phthalimidoacetyl chloride (175 mg, 0.78 mmol), and the mixture was stirred for 15 minutes at room temperature. To this solution was added pyridine (0.08 mL), and the mixture was stirred for 15 minutes at room temperature. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate. The aqueous layer was separated, and the organic layer was washed with water and a saturated aqueous solution of sodium chloride, which was dried over magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was crystallized from ethanol to give 138 mg (yield 43%) of the titled compound, m.p. 241°-242.5° C.

Workup

  1. stirringthe mixture was stirred for 15 minutes at room temperature
  2. customThe aqueous layer was separated
  3. washthe organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, which was dried over magnesium sulfate
  5. filtrationfollowed by filtration and concentration under reduced pressure
  6. customThe concentrate was crystallized from ethanol

Sources & evidence

ORD record
ord-935dddf3cef94843be6745bc9c6041a3
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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