alpha-(3,4-Dimethoxyphenyl)benzeneethanamine → (R)-N-[1-(3,4-dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(tetrazolo[1,5-a]pyrid-6-yl)-ethylamine

HRID 861443Notes

Reaction equation

HRID 861443 reaction equation
[N:1]1[N:2]=[N:3][N:4]2[CH:9]=[C:8]([C@@H:10]3[CH2:12][O:11]3)[CH:7]=[CH:6][C:5]=12.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:23]([NH2:31])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]>CO>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:23]([NH:31][CH2:12][C@H:10]([OH:11])[C:8]2[CH:7]=[CH:6][C:5]3[N:4]([N:3]=[N:2][N:1]=3)[CH:9]=2)[CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 411116alpha-(3,4-Dimethoxyphenyl)benzeneethanamineHCID 13090314(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxirane

Product 1

HCID 22881913(R)-N-[1-(3,4-dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(tetrazolo[1,5-a]pyrid-6-yl)-ethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.178 g (1 mmol) of (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane (see Fisher and Wyvratt, EP 0 318 092 A2 for the synthesis of this compound) and 0.518 g (2 mmol) of α-(3,4-dimethoxyphenyl) benzeneethanamine in dry methanol (10 mL) was heated at reflux in a gas tight vessel for 14 hours. The reaction mixture was concentrated and the residue was chromatographed on silica gel (5% methaol in methylene chloride) to give the product as a white solid: 1H NMR (500 MHz, CDCl3)δ 8.76 (d, 1H, J=15 Hz), 7.91 (dd, 1H, J=9, 3 Hz), 7.41 (t, 1H, J=11 Hz), 7.10-7.32 (m, 5H), 6.77-6.83 (m, 3H), 4.51-4.73 (m, 1H), 3.89 (s, 3H. OCH3), 3.88 and 3.86 (s, 3H, OCH3), 3.74-3.89 (m, 1H), 2.96-3.0 (m, 1H), 2.84-2.92 (m, 2H), 2.94-2.61 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux in a gas tight vessel for 14 hours
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was chromatographed on silica gel (5% methaol in methylene chloride)

Sources & evidence

ORD record
ord-52c58ec102744984bd7662045831bcbd
Source dataset
uspto-grants-1998_02
Patent number
US05714506

Reaction notes

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