Sodium Bicarbonate → 8-{4-[2-(7-Methoxy-1-benzofuran-3-yl)-1-methylethyl)piperazin-1-yl]quinoline

HRID 1178827Notes

Reaction equation

HRID 1178827 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][C:13]([CH3:15])=O)[C:7]=2[CH:6]=[CH:5][CH:4]=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[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH:13]([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)[CH3:15])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 118307868-(1-piperazinyl)QuinolineHCID 236144341-(7-Methoxy-1-benzofuran-3-yl)propan-2-one

Product 1

HCID 111655288-{4-[2-(7-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-(7-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, the 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 yellow oil. Yield: 60 mg (14%); (M+H): 402; 1HNMR (400 MHz, CDCl3): δ 8.90˜8.14 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H); 8.13˜7.56 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H); 7.46˜6.80 (m, 8H); 4.01 (s, 3H); 3.51˜1.60 (m, 11H); 1.14(d, J=6.0 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-c6cea6096bc64987b5e756054faecd5a
Source dataset
uspto-grants-2007_10
Patent number
US07276603B2

Reaction notes

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