Phenethylamine → HCID 10055192, compound

HRID 1707326Notes

Reaction equation

HRID 1707326 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][S:21][C:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:10][NH:11][C@H:12]([C:17]([OH:19])=O)[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)CCCN=C=NCC.ON1C(=O)C2C=CC=CC=2N=N1.[CH2:64]([NH2:72])[CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1.C(N(C(C)C)CC)(C)C>CCOC(C)=O.C(Cl)(Cl)Cl>[CH2:64]([NH:72][C:17](=[O:19])[C@H:12]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH:11][CH2:10][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:20][S:21][C:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Participants

7

Reactant 5

HCID 1001PhenethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 81531DiisopropylethylamineHCID 10347845HCID 10347845, compound

Product 1

HCID 10055192HCID 10055192, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 21584013Chloroform ethylacetateSolvent

Procedure

The product of Step C (0.108 g, 0.2 mmol), 1-(3-dimethylaminopropyl )-3-ethylcarbodiimide (EDC) (0.042 g, 0.22 mmol), and 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine (HOOBT) (0.036g, 0.22 mmol) were dissolved in 4 mL of 1:1 EtOAc/CHCl3 and stirred at ambient temperature for 0.5 hr. To this yellow solution was added phenethylamine (0.028 mL, 0.22 mmol) and diisopropylethylamine (0.038 mL, 0.22 mmol) and stirring was continued for 48 h. The solution was concentrated and the residue was partitioned between EtOAc and H2O. The organic layer was washed with water, aqueous saturated NaHCO3, brine, and dried (Na2SO4). Filtration and concentration followed by chromatography (SiO2, EtOAc: hexane, 1:3) gave 0.09 g (69%) of the title compound.

Workup

  1. stirringstirring
  2. waitwas continued for 48 h
  3. concentrationThe solution was concentrated
  4. customthe residue was partitioned between EtOAc and H2O
  5. washThe organic layer was washed with water, aqueous saturated NaHCO3, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-7329be93ff6e4dc6af7a0bbeec81117f
Source dataset
uspto-grants-1994_10
Patent number
US05352705

Reaction notes

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