Sodium Bicarbonate → 8-{4-[2-(5-Methoxy-1-benzofuran-3-yl)-1-methylethyl)piperazin-1-yl]quinoline

HRID 1178831Notes

Reaction equation

HRID 1178831 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[C:8]([CH2:11][C:12]([CH3:14])=O)[C:7]=2[CH:15]=1.[N:16]1([C:22]2[CH:23]=[CH:24][CH:25]=[C:26]3[C:31]=2[N:30]=[CH:29][CH:28]=[CH:27]3)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[C:8]([CH2:11][CH:12]([N:19]3[CH2:20][CH2:21][N:16]([C:22]4[CH:23]=[CH:24][CH:25]=[C:26]5[C:31]=4[N:30]=[CH:29][CH:28]=[CH:27]5)[CH2:17][CH2:18]3)[CH3:14])[C:7]=2[CH:15]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 118307868-(1-piperazinyl)QuinolineHCID 156187201-(5-Methoxy-1-benzofuran-3-yl)propan-2-one

Product 1

HCID 112350168-{4-[2-(5-Methoxy-1-benzofuran-3-yl)-1-methylethyl)piperazin-1-yl]quinoline

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

To a stirred mixture of 1-(5-methoxy-1-benzofuran-3-yl)acetone (204 mg, 1 mmol) and 8-piperazino quinoline (213.0 mg, 1 mmol) in 1,2-dichloroethane (100 ml) and acetic acid (1 ml), sodium triacetoxyborohydride (422 mg, 2 mmol) was added at room temperature. Reaction mixture was stirred at room temperature for 72 hrs. At the end, reaction mixture was neutralized with 10% NaHCO3 and extracted with chloroform. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The product obtained was purified by silica-gel column chromatography by eluting it initially with 80% ethyl acetate:hexane and then with 5% methanol:ethyl acetate, yielding a brown semi-solid. Yield: 60 mg (14%); (M+H): 402; 1HNMR (400 MHz, CDCl3): δ 8.90˜8.88 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H); 8.13˜8.10 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H); 7.60˜6.70 (m, 8H); 3.87 (s, 3H); 3.50˜2.50 (m, 11H); 1.15˜1.13 (d, J=6.0 Hz, 3H).

Workup

  1. additionwas added at room temperature
  2. customReaction mixture
  3. customAt the end, reaction mixture
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product obtained
  9. customwas purified by silica-gel column chromatography
  10. washby eluting it initially with 80% ethyl acetate
  11. customhexane and then with 5% methanol:ethyl acetate, yielding a brown semi-solid

Sources & evidence

ORD record
ord-d7827eaa67da44fa860917d4f33f5e36
Source dataset
uspto-grants-2007_10
Patent number
US07276603B2

Reaction notes

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