Cyclohexylamine → 2-[2-Phenyl-2-(diethylamino)-ethenyl]-3,4,5,6-tetrahydropyridine

HRID 66167Notes

Reaction equation

HRID 66167 reaction equation
C(O[C:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:5][C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]=1)C.F[B-](F)(F)F.C1(N)CCCCC1.C1(C(NC2CCCCC2)=[CH:37][C:38]2CC[CH2:41][CH2:40][N:39]=2)C=CC=CC=1.CS([O-])(=O)=O>C(NCC)C>[C:12]1([C:4]([N:39]([CH2:40][CH3:41])[CH2:38][CH3:37])=[CH:5][C:6]2[CH2:11][CH2:10][CH2:9][CH2:8][N:7]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 85257MethanesulfonateHCID 867362192-(2-Ethoxy-2-phenyl-ethenyl)-3,4,5,6-tetrahydropyridine tetrafluoroborate2×HCID 178463269HCID 178463269, compound

Product 1

HCID 539011482-[2-Phenyl-2-(diethylamino)-ethenyl]-3,4,5,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 8021DiethylamineSolvent

Procedure

Analogously to Example 1, there is obtained, starting with 9.5 g of 2-(2-ethoxy-2-phenyl-ethenyl)-3,4,5,6-tetrahydropyridine-tetrafluoroborate and 30 ml of cyclohexylamine, 2-[(2-phenyl-2-(cyclohexylamino)-ethenyl]-3,4,5,6-tetrahydropyridine, and from this its (1:1)-methanesulphonate, m.p. 172°-173°; and starting with 9.5 g of 2-(2-ethoxy-2-phenyl-ethenyl)-3,4,5,6-tetrahydropyridine-tetrafluoroborate and 30 ml of diethylamine, is obtained 2-[2-phenyl-2-(diethylamino)-ethenyl]-3,4,5,6-tetrahydropyridine, and from this its (1:1)-fumarate, m.p. 169°-170° (from isopropanol).

Workup

  1. customAnalogously to Example 1, there is obtained

Sources & evidence

ORD record
ord-16d427ede03343c3b3d0734e3049c9e8
Source dataset
uspto-grants-1978_12
Patent number
US04130652

Reaction notes

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