[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone → 4-(2-(Piperidin-1-yl)ethoxy)benzaldehyde

HRID 2223673Notes

Reaction equation

HRID 2223673 reaction equation
COC1C=CC=CC=1C[Mg]Cl.CN(C)C1SC2C=C(OC)C=CC=2C=1[C:25]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:29][CH:28]=1)=[O:26]>C1COCC1>[N:36]1([CH2:35][CH2:34][O:33][C:30]2[CH:29]=[CH:28][C:27]([CH:25]=[O:26])=[CH:32][CH:31]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 9954835[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneHCID 178489472HCID 178489472, compound2×

Product 1

HCID 111838924-(2-(Piperidin-1-yl)ethoxy)benzaldehydeYield 257.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add a solution of 2-methoxybenzylmagnesium chloride (5 mL of 0.25 M/THF) to a stirred solution of (2-dimethylamino-6-methoxy-benzo[b]thiophen-3-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (500 mg, 1.14 mmol) in THF (5 mL) at −78° C. After 30 min, add additional 2-methoxybenzyl-magnesium chloride (5 mL). After 30 min, quench with water and dilute with iPrOH/CHCl3(1:3). Wash the organic phase with water and brine, dry over MgSO4, filter and concentrate to yield 6-methoxy-2-(2-methoxy-benzyl)-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (686 mg). Use the crude product without further purification.

Workup

  1. waitAfter 30 min
  2. customquench with water
  3. additiondilute with iPrOH/CHCl3(1:3)
  4. washWash the organic phase with water and brine
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-8bbe9dd32fa046559f548393fe9388e5
Source dataset
uspto-grants-2008_05
Patent number
US07375229B2

Reaction notes

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