Benzene → HCID 20357471, compound

HRID 2083757Notes

Reaction equation

HRID 2083757 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[C:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:4]=2[CH:3]=1.[CH:22]1[CH:27]=[CH:26][CH:25]=[CH:24]C=1.C1(C(Cl)=O)CCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[C:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH:27]4[CH2:24][CH2:25][CH2:26]4)[CH2:18][CH2:17]3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 241Benzene2×HCID 78705Cyclobutanecarbonyl chlorideHCID 133194264-(2-Chloro-9H-thioxanthen-9-ylidene)piperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 20357471HCID 20357471, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Similarly, 6.3 g. (0.02 mol) of 4-(2-chloro-9-thioxanthenylidene)piperidine in 30 ml. of benzene is treated with a solution of 1.2 g. (0.01 mol) of cyclobutylcarboxylic acid chloride in 10 ml. of benzene. Following the above workup procedure, the intermediate amide is reduced with 1.5 g. (0.04 mol) of lithium aluminum hydride in 50 ml. of ether. After isolation of the amine product, the ether is evaporated in vacuo and a hexamate salt formed of 4-(2-chloro-9-thioxanthenylidene)-1-cyclobutylmethylpiperidine, m.p. 180°-182° C.

Workup

  1. customAfter isolation of the amine product, the ether is evaporated in vacuo

Sources & evidence

ORD record
ord-e01276bb37d24998ae18da908969d794
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

Loading…