Sodium triacetoxyborohydride → 6-Methoxy-8-{4-[2-(7-methoxy-1-benzofuran-3-yl)-1-methylethyl)piperazin-1-yl]quinoline

HRID 1178828Notes

Reaction equation

HRID 1178828 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.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[C:26]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:27]=1)[N:24]=[CH:23][CH:22]=[CH:21]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[C:26]([N:28]3[CH2:29][CH2:30][N:31]([CH:13]([CH3:15])[CH2:12][C:8]4[C:7]5[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=5[O:10][CH:9]=4)[CH2:32][CH2:33]3)[CH:27]=1)[N:24]=[CH:23][CH:22]=[CH:21]2

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 184141776-Methoxy-8-(piperazin-1-YL)quinolineHCID 236144341-(7-Methoxy-1-benzofuran-3-yl)propan-2-one

Product 1

HCID 113394396-Methoxy-8-{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

6-methoxy-8-{4-[2-(7-methoxy-1-benzofuran-3-yl)-1-methylethyl)piperazin-1-yl]quinoline was prepared by generally following the procedure outlined in example 35, step 2, starting from the 1-(7-methoxy-1-benzofuran-3-yl)acetone (204 mg, 1 mmol) and 6-methoxy-8-piperazino quinoline (243.0 mg, 1 mmol) in 1,2-dichloroethane (100 ml) and acetic acid (1 ml), sodium triacetoxyborohydride (422 mg, 2 mmol). The product 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: 75 mg (17%); (M+H): 432.

Workup

  1. customThe product was purified by silica-gel column chromatography
  2. washby eluting it initially with 80% ethyl acetate
  3. customhexane and then with 5% methanol:ethyl acetate, yielding a brown semi-solid

Sources & evidence

ORD record
ord-be888245b4984c509d9499d6c40867c1
Source dataset
uspto-grants-2007_10
Patent number
US07276603B2

Reaction notes

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