Sodium Hydroxide → HCID 24983469, compound

HRID 453723Notes

Reaction equation

HRID 453723 reaction equation
[CH2:1]([N:8]([CH3:21])[C:9](=O)/[CH:10]=[C:11]1\[CH2:12][CH2:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][C:19]\1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[CH2:1]([N:8]([CH3:21])[CH2:9]/[CH:10]=[C:11]1\[CH2:12][CH2:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][C:19]\1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57855419HCID 57855419, compound

Product 1

HCID 24983469HCID 24983469, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(E)-N-benzyl-2-(6,7-dihydrobenzo[b]thiophen-4(5H)-ylidene)-N-methylacetamide (0.32 g, 1.01 mmol) in THF anh. (5 mL) is added slowly to a suspension of AlLiH4 (0.1 g, 2.63 mmol) in THF anh. (20 mL) cooled in an ice bath and is stirred at room temperature for 1 hour and refluxed for 2 hours. The solution is cooled in an ice bath and some drops of NaOH 10% is added. The mixture is filtered and washed with ethyl acetate. The filtrate is evaporated to dryness and the residue is dissolved in ethyl acetate and washed with water. The organic phase is removed and the resulting crude is purified by column chromatography, giving (E)-N-benzyl-2-(6,7-dihydrobenzo[b]thien-4(5H)-ylidene)-N-methylethanamine (0.25 g, 0.88 mmol, 87%, oil). 1H NMR (300 MHz, CDCl3): δ 1.90 (m, 2H), 2.29 (s, 3H), 2.44 (m, 2H), 2.84 (t, J=6.1 Hz, 2H), 3.26 (d, J=7.0 Hz, 2H), 3.62 (s, 2H), 5.94 (t, J=7.0 Hz, 1H), 7.04 (d, J=5.3 Hz, 1H), 7.20 (d, J=5.3 Hz, 1H), 7.25-7.40 (m, 5H).

Workup

  1. temperaturecooled in an ice bath
  2. temperaturerefluxed for 2 hours
  3. temperatureThe solution is cooled in an ice bath
  4. filtrationThe mixture is filtered
  5. washwashed with ethyl acetate
  6. customThe filtrate is evaporated to dryness
  7. dissolutionthe residue is dissolved in ethyl acetate
  8. washwashed with water
  9. customThe organic phase is removed
  10. customthe resulting crude is purified by column chromatography

Sources & evidence

ORD record
ord-82df4d0bdde54c4991465d61b4838ef8
Source dataset
uspto-grants-2013_07
Patent number
US08492563B2

Reaction notes

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