[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone → [2-(2-[1,3]Dioxolan-2-yl-phenyl)-6-methoxy-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

HRID 916855Notes

Reaction equation

HRID 916855 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Mg]Br.CN(C)[C:16]1[S:20][C:19]2[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:18]=2[C:17]=1[C:27]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][N:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:31][CH:30]=1)=[O:28]>C1COCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:16]1[S:20][C:19]2[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:18]=2[C:17]=1[C:27]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][N:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:31][CH:30]=1)=[O:28]

Participants

4

Reactant 2

HCID 9954835[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneHCID 178419622HCID 178419622, compound

Product 1

HCID 17987059[2-(2-[1,3]Dioxolan-2-yl-phenyl)-6-methoxy-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add a solution of 2-(1,3-dioxolan-2-yl)phenylmagnesium bromide (15 mL of 0.5 M/THF, 7.5 mmol) to a stirred solution of (2-dimethylamino-6-methoxy-benzo[b]thiophen-3-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (650 mg, 1.48 mmol) in THF (5 mL) at r.t. Stir the reaction mixture at r.t. for 2 h and quench with aq. NaHCO3. Dilute with CH2Cl2 and wash with water and brine, dry over MgSO4, filter and concentrate to afford [2-(2-[1,3]dioxolan-2-yl-phenyl)-6-methoxy-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone. Use the product without further purification.

Workup

  1. customquench with aq. NaHCO3
  2. additionDilute with CH2Cl2
  3. washwash with water and brine
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-a74d8f30953948babdc58e3cc81ca08b
Source dataset
uspto-grants-2007_09
Patent number
US07271264B2

Reaction notes

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