Phenethyl bromide → 9-(2-Phenylethyl)-2,3,9,10a-tetrahydrobenzo[b]-cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 356198Notes

Reaction equation

HRID 356198 reaction equation
[CH2:1]1[CH:10]2[C:4](=[N:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][C:9]2=[O:11])[CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>CN(C)C=O.O>[C:21]1([CH2:20][CH2:19][N:8]2[C:9](=[O:11])[CH:10]3[CH2:1][CH2:2][CH2:3][C:4]3=[N:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]2=3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 123949352,3,9,10a-Tetrahydro-1H-benzo[b]cyclopenta[f][1,4]diazepin-10-one

Product 1

HCID 189405749-(2-Phenylethyl)-2,3,9,10a-tetrahydrobenzo[b]-cyclopenta[e][1,4]diazepin-10(1H)-oneYield 31.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2,3,9,10a-tetrahydrobenzo[b]-cyclopenta[e][1,4]diazepin-10(1H)-one (5.01 g, 25 mmol) in N,N-dimethylformamide (30 mL) was cooled to 0° C. To the solution was added sodium hydride (60% liquid paraffin dispersion, 1.0 g, 25 mmol). The mixture was stirred for 5 minutes at the same temperature and for 10 minutes at room temperature. To this solution was added a solution of 2-(bromoethyl)benzene (5.09 g, 27.5 mmol) in N,N-dimethylformamide (1 mL), and the mixture was stirred for 2.5 hours at room temperature. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride (40 mL), which was diluted with water, followed by extraction twice with ethyl acetate. Organic layers were combined and washed with water and a saturated aqueous solution of sodium chloride, which was dried by allowing to pass through magnesium sulfate and silica-gel, followed by concentration under reduced pressure. Unreacted diazepinone was allowed to crystallize, and most portion of which was removed. The remainder was purified by silica-gel column chromatography (hexane-ethyl acetate 20:1, later 5:1), followed by recrystallization from ethyl acetate-hexane to afford the titled compound (2.37 g, 31%), m.p.101°-102° C.

Workup

  1. stirringthe mixture was stirred for 2.5 hours at room temperature
  2. extractionfollowed by extraction twice with ethyl acetate
  3. washwashed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, which was dried
  5. concentrationfollowed by concentration under reduced pressure
  6. customto crystallize
  7. custommost portion of which was removed
  8. customThe remainder was purified by silica-gel column chromatography (hexane-ethyl acetate 20:1, later 5:1),
  9. customfollowed by recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a94a5f84f29544c89c76bb7f0cc8c439
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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