Pyridine → HCID 178448009, compound

HRID 1731278Notes

Reaction equation

HRID 1731278 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:23](C#N)#[N:24].N1C=CC=CC=1.CN1CCCC1=O>Cl>[C:23]([C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)#[N:24]

Participants

6

Reactant 4

HCID 1049PyridineHCID 9999CyanogenHCID 13387N-methyl-2-pyrrolidoneHCID 178448002HCID 178448002, compound

Product 1

HCID 178448009HCID 178448009, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 36.3 g of trans-1-p-bromophenyl-4-(trans-4-propylcyclohexyl)-cyclohexane, 10 g of Cu2 (CN)2, 120 ml of pyridine and 60 ml of N-methylpyrrolidone is heated to 160° for 2 hours. The mixture is cooled, a solution of 120 g of FeCl3.6H2O in 600 ml of 20% hydrochloric acid and the mixture is warmed to 70° for 1.5 hours, while stirring, and worked up in the customary manner to give trans-1-p-cyanophenyl-4-(trans-4-propylcyclohexyl)-cyclohexane, m.p. 55°, c.p. 184°.

Workup

  1. temperatureis heated to 160° for 2 hours
  2. temperatureThe mixture is cooled

Sources & evidence

ORD record
ord-167ff1a523414092a280588e5e8ddf08
Source dataset
uspto-grants-1986_11
Patent number
US04620938

Reaction notes

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