Ammonia → HCID 53876213, compound

HRID 487103Notes

Reaction equation

HRID 487103 reaction equation
Cl.[CH3:2][N:3]1[CH2:12][CH2:11][C:10]2[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH2:7][CH2:6][C:5]=2[CH2:4]1.[Li].N.NC1C=CC=CC=1>C1COCC1>[CH3:2][N:3]1[CH2:12][CH2:11][C@@H:10]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=32)[CH2:4]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6115AnilineHCID 3028194LithiumHCID 19093642HCID 19093642, compound

Product 1

HCID 53876213HCID 53876213, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure of Example 2, 0.64 g (2.71 mmol) of 1,2,3,4,5,6-hexahydro-3-methyl-benz[f]isoquinoline hydrochloride was reacted with 0.126 g of lithium wire in 100 ml of liquid ammonia, 25 ml of anhydrous THF and 0.25 ml of aniline. Chromatography on flash silica, eluting with 5-10% methanol/dichloromethane, then on alumina, eluting with 25% ethyl acetate/petroleum ether gave 0.340 g (62%) of the title product as a colourless oil. The hydrochloride salt was made using ethereal hydrogen chloride. Upon evaporation of the solvent, the title product hydrochloride was obtained as a white solid, m.p. 277°-285° C. (dec). NMR δ(D2O) 1.52-1.92 (4H, m), 2.63-2.75 (2H, m), 2.86-2.98 (3H, m), 2.92 (3H, s), 3.19 (1H, t of d, J=13 and 3 Hz), 3.56 (1H, m), 7.22-7.28 (3H, m), 7.33-7.36 (1H, m). m/z (CI+, NH3) 202 (M+H)+.

Workup

  1. washChromatography on flash silica, eluting with 5-10% methanol/dichloromethane
  2. washon alumina, eluting with 25% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-399736a01dde434e9bd6867a82545e24
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

Loading…