Gramine → HCID 9948843, compound

HRID 1900703Notes

Reaction equation

HRID 1900703 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([CH2:18][C:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[NH:21][CH:20]=1)C>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8][C:9]2[CH2:14][CH2:13][N:12]([CH2:18][C:19]3[C:23]4[C:22](=[CH:27][CH:26]=[CH:25][CH:24]=4)[NH:21][CH:20]=3)[CH2:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6890GramineHCID 21473648HCID 21473648, compound

Product 1

HCID 9948843HCID 9948843, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(2-phenylethyl)-1,2,3,6-tetrahydropyridine (prepared by the method of Oediger and Joop, Leibigs. Ann. Chem., 972, 764, 21) (400 mg, 2.2 mmol) in dry toluene (10ml) was added gramine (370 mg, 2.1 mmol) and the reaction heated at reflux overnight. The solvent was evaporated and the residue chromatographed on silica gel eluting with 2% Et3N/EtOAc to give a solid which was recrystallised twice from toluene to yield the title compound as a white solid (160 mg, 25%), m.p. 138-140° C.; (Found: C, 83.59; H, 7.71; N, 8.89. C22H24N2 requires C, 83.50; H, 7.64; N, 8.85%); δH (CDCl3) 2.13 (2H, br s, tetrahydropyridinyl CH2), 2.25 (2H, t, J 8.3 Hz, PhCH2CH2), 2.64-2.73 (4H, m, tetrahydropyridinyl CH2, PhCH2CH2), 3.05 (2H, br s, tetrahydropyridinyl CH2), 3.81 (2H, s, NCH2Ar), 5.40 (1H, br s, tetrahydropyridyl CH), 7.11-7.28 (8H, m, ArH), 7.36 (1H, d, J 7.9 Hz, ArH), 7.72 (1H, d, J 7.9 Hz, ArH), and 8.12 (1H, br s, NH); m/z (CI+, NH3) 317 (M+1)+.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated
  4. customthe residue chromatographed on silica gel eluting with 2% Et3N/EtOAc
  5. customto give a solid which
  6. customwas recrystallised twice from toluene

Sources & evidence

ORD record
ord-80ad7b45512f4f58b50dab336917a71d
Source dataset
uspto-grants-1996_11
Patent number
US05576336

Reaction notes

Loading…