Phenethylamine → HCID 68619645, compound

HRID 1159355Notes

Reaction equation

HRID 1159355 reaction equation
[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3]1.[CH2:9](CN)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:18]([N:20](CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[CH2:9]([N:20]([CH3:18])[C:6]([CH:4]1[CH2:3][C:2](=[O:1])[CH2:5]1)=[O:8])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 68619645HCID 68619645, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acid, 3-oxocyclobutanecarboxylic acid (12.7 g, 0.11 mol), N-benzylmethylamine (15.7 mL, 0.12 mol), and triethylamine (48 mL, 0.33 mol) were dissolved in DMF (100 mL). BOP (49 g, 11 mol) was added at 0° C. under stirring in argon. The mixture was stirred at 20° C. for 20 h, evaporated, and the residue was dried at 0.5 mmHg. The residue was purified by chromatography (silica gel, 63-100 μm, 750 mL, CCl4→CHCl3, CHCl3/MeOH 100:0→95:5). The title compound (15.5 g, 64%) was obtained as a colorless oil. 1H NMR-data (DMSO-d6): 7.20 (m, 5H, Ph); 4.62 s, 4.55 s (2H, CH2); 3.46-3.62 (m, 1H); 3.28 (m, 4H,); 2.85 s, 2.94 s (3H, NCH3).

Workup

  1. stirringThe mixture was stirred at 20° C. for 20 h
  2. customevaporated
  3. customthe residue was dried at 0.5 mmHg
  4. customThe residue was purified by chromatography (silica gel, 63-100 μm, 750 mL, CCl4→CHCl3, CHCl3/MeOH 100:0→95:5)

Sources & evidence

ORD record
ord-1e003e7212fe430ea6d7a90e3ad83eb1
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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