Hydrochloric Acid → 2-Imino-5-phenyl-5-cyclohexyltetrahydrofuran hydrochloride

HRID 1074150Notes

Reaction equation

HRID 1074150 reaction equation
[C:1]1([C:7]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)([OH:12])[CH2:8][CH2:9][C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:19]>O1CCCC1.CCOCC>[ClH:19].[NH:11]=[C:10]1[CH2:9][CH2:8][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[O:12]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 221558721-Phenyl-1-cyclohexyl-3-cyano-1-propanol

Product 1

HCID 221558852-Imino-5-phenyl-5-cyclohexyltetrahydrofuran hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of 1-phenyl-1-cyclohexyl-3-cyano-1-propanol (1.4 g) in anhydrous tetrahydrofuran (THF), a solution of HCl 10% w/v in ether (2.5 ml) was added dropwise. The mixture was stirred and cooled for 48 hours. The solvent was removed and the residue triturated with diethyl ether/THF to afford 0.8 g of 2-imino-5-phenyl-5-cyclohexyltetrahydrofuran hydrochloride. M.p. 100°-102° C.

Workup

  1. additionwas added dropwise
  2. temperaturecooled for 48 hours
  3. customThe solvent was removed
  4. customthe residue triturated with diethyl ether/THF

Sources & evidence

ORD record
ord-21febca478d54413b40506947ec8595f
Source dataset
uspto-grants-1990_11
Patent number
US04973592

Reaction notes

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