Benzene, (2-bromoethoxy)- → HCID 22396720, compound

HRID 1370479Notes

Reaction equation

HRID 1370479 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[CH:11]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18][CH:12]3[NH:13][C:14]=2[CH:15]=[CH:16][CH:17]=1.[C:30]1([O:36][CH2:37][CH2:38]Br)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[CH:11]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18][CH:12]3[N:13]([CH2:38][CH2:37][O:36][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 68526Benzene, (2-bromoethoxy)-HCID 516892Sodium BicarbonateHCID 22396753HCID 22396753, compound

Product 1

HCID 22396720HCID 22396720, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 10-(2,4-dichlorophenyl)-1,4,5,5a,6,10b-hexahydroazepino[4,5-b]indole-3(2H)-carboxylate (54 mg) in DMF (1.2 ml) was added KH (10 mg) and 2-bromoethyl phenyl ether (30 mg). The reaction mixture was stirred 24 h, poured into satd NaHCO3, extracted with CH2Cl2, dried over MgSO4, filtered and concentrated. Purification via flash chromatography provided the title compound: 1H NMR (CDCl3) δ 1.63, 2.30-2.50, 2.92, 3.14, 3.42, 3.75, 4.26, 4.53, 6.84, 6.96, 7.20-7.51.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification via flash chromatography

Sources & evidence

ORD record
ord-93ed9059b3f14e1a967458a0ea510c61
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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