Phenethylamine → HCID 58677376, compound

HRID 747543Notes

Reaction equation

HRID 747543 reaction equation
[CH:1]([C:3]1[S:7][C:6]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=O.C(OC)(OC)OC.[CH2:24]([NH2:32])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[BH4-].[Na+]>CO>[CH2:24]([NH:32][CH2:1][C:3]1[S:7][C:6]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 9005Trimethyl orthoformateHCID 4311764Sodium borohydrideHCID 58677388HCID 58677388, compound

Product 1

HCID 58677376HCID 58677376, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 4-(5-formyl-thiophen-2-yloxy)-benzonitrile (200 mg, 0.87 mmol), (MeO)3CH (1.2 mL), phenethyl amine (0.142 mL, 130 mol %) and methanol (1.7 mL). Stir the resulting mixture for 3 hours, and then add sodium borohydride in portions. Stir for few hours. Then, concentrate to remove the methanol. Partition the resulting residue between H2O (5 mL) and CH2Cl2 (7 ml). Dry the organic layer over sodium sulfate, filter and concentrate. Purify the product through flash chromatography [CH2Cl2/Ammonia (2.0 M in methanol) 20/1] to provide the title compound (139 mg, 48%).

Workup

  1. stirringStir for few hours
  2. concentrationThen, concentrate
  3. customto remove the methanol
  4. customPartition the resulting residue between H2O (5 mL) and CH2Cl2 (7 ml)
  5. dry with materialDry the organic layer over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the product through flash chromatography [CH2Cl2/Ammonia (2.0 M in methanol) 20/1]

Sources & evidence

ORD record
ord-e27dca16520f49a39743ccffaaa760c4
Source dataset
uspto-grants-2008_07
Patent number
US07396943B2

Reaction notes

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