Sodium hydride → HCID 70110276, compound

HRID 356191Notes

Reaction equation

HRID 356191 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.C(=O)([O-])O.[Na+].[C:19]1(=[O:47])[N:23]([CH2:24][C:25]([N:27]2[C@@H:33]3[CH2:34][CH2:35][CH2:36][C@@H:32]3[C:31](=[O:37])[NH:30][C:29]3[CH:38]=[CH:39][CH:40]=[CH:41][C:28]2=3)=[O:26])[C:22](=[O:42])[C:21]2=[CH:43][CH:44]=[CH:45][CH:46]=[C:20]12.[H-].[Na+]>O.C(OCC)(=O)C.CN(C)C=O>[C:22]1(=[O:42])[N:23]([CH2:24][C:25]([N:27]2[C@@H:33]3[CH2:34][CH2:35][CH2:36][C@@H:32]3[C:31](=[O:37])[N:30]([CH2:3][C:4]3[CH:13]=[CH:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)[C:29]3[CH:38]=[CH:39][CH:40]=[CH:41][C:28]2=3)=[O:26])[C:19](=[O:47])[C:20]2=[CH:46][CH:45]=[CH:44][CH:43]=[C:21]12

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 70111957HCID 70111957, compound

Product 1

HCID 70110276HCID 70110276, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(Chloromethyl)quinoline hydrochloride (321 mg, 1.5 mmol) was dissolved in water (0.5 mL) and ethyl acetate (1 mL), which was neutralized with sodium hydrogencarbonate. The organic layer was separated, and the aqueous layer was subjected to extraction twice with ethyl acetate. The organic layers were combined and dried over magnesium sulfate, which was concentrated under reduced pressure. To the concentrate were added (3aR*,10aS*)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]-cyclopenta[e][1,4]diazepin-10(1H)-one (390 mg, 1.0 mmol) and N,N-dimethylformamide (3 mL). To this suspension was added, at 0° C., sodium hydride (60% liquid paraffin dispersion, 48 mg, 1.2 mmol), and the mixture was stirred for 20 minutes at room temperature. To the reaction mixture was added water, which was subjected to extraction twice with chloroform. Organic layers were combined, washed with water, dried over magnesium sulfate, subjected to filtration and, then, concentrated under reduced pressure. The concentrate was crystallized from ethanol-hexane to give 243 mg (yield 46%) of the titled compound, m.p. 258°-260° C.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was subjected to extraction twice with ethyl acetate
  3. dry with materialdried over magnesium sulfate, which
  4. concentrationwas concentrated under reduced pressure
  5. additionTo this suspension was added, at 0° C.
  6. extractionwas subjected to extraction twice with chloroform
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationsubjected to filtration
  10. concentrationconcentrated under reduced pressure
  11. customThe concentrate was crystallized from ethanol-hexane

Sources & evidence

ORD record
ord-26b71a886e2e44efb6795b7a035b95c9
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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