Phenethylamine → HCID 11515703, compound

HRID 1943612Notes

Reaction equation

HRID 1943612 reaction equation
[C:1]1([N:7]2[C:15]3[CH2:14][CH2:13][CH2:12]/[C:11](=[CH:16]\[CH:17]=O)/[C:10]=3[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19](CN)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:28]([BH3-])#[N:29].[Na+]>CO>[CH2:19]([N:29]([CH3:28])[CH2:17]/[CH:16]=[C:11]1/[C:10]2[CH:9]=[N:8][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:15]=2[CH2:14][CH2:13][CH2:12]/1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 5003444Sodium cyanoborohydrideHCID 59553058HCID 59553058, compound

Product 1

HCID 11515703HCID 11515703, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (E)-2-(1,5,6,7-tetrahydro-1-phenyl-4H-indazol-4-ylidene) acetaldehyde (299 mg, 1.25 mmol) and N-benzylmethylamine (0.18 mL, 1.38 mmol) in methanol (20 mL) cooled to 0° C. is left stirring for 20 minutes. Then sodium cyanoborohydride (213 mg, 3.39 mmol) at 0° C. is added, and then it is left to increase to room temperature following the TLC reaction. The solvent is evaporated at reduced pressure, diluted in ethyl acetate, washed with water and with sodium chloride saturated solution, dried and evaporated under reduced pressure. The resulting crude product is purified by means of silica gel chromatography, giving (E)-N-benzyl-2-(6,7-dihydro-1-phenyl-1H-indazol-4(5H)-ylidene)-N-methylethanamine (158 mg, 0.46 mmol, 36%, oil).

Workup

  1. waitis left
  2. waitit is left
  3. customthe TLC reaction
  4. customThe solvent is evaporated at reduced pressure
  5. additiondiluted in ethyl acetate
  6. washwashed with water and with sodium chloride saturated solution
  7. customdried
  8. customevaporated under reduced pressure
  9. customThe resulting crude product is purified by means of silica gel chromatography

Sources & evidence

ORD record
ord-ef47fffd612f427ba9b1ab9aa3c747d1
Source dataset
uspto-grants-2013_03
Patent number
US08394797B2

Reaction notes

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