Octyl isothiocyanate → HCID 20291246, compound

HRID 1413951Notes

Reaction equation

HRID 1413951 reaction equation
[CH2:1]([N:9]=[C:10]=[S:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:12]1([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[C:12]1([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]2[CH2:20][CH2:21][N:22]([C:10](=[S:11])[NH:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:23][CH2:24]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 78161Octyl isothiocyanateHCID 882784-Benzhydrylpiperidine

Product 1

HCID 20291246HCID 20291246, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 6.0 g (0.035 mole) of n-octylisothiocyanate was dissolved in 25 ml of toluene, treated with 8.80 g (0.035 mole) of 4-diphenylmethylpiperidine and stirred at 25° for twelve hours. The mixture was cooled, filtered and evaporated. Chromatography of the residue through silica gel using chloroform as an eluent afforded a brown oil, 4-(diphenylmethyl)-N-octyl-1- piperidinecarbothioamide. A mixture of 1.0 g (0.0024 mole) of this material, 3 g of Raney Nickel and 15 ml of isopropanol was refluxed three hours, cooled, and filtered. Evaporation of the filtrate afforded an oil which was converted to a fumarate identified as 4-(diphenylmethyl)- 1-[(octylimino)methyl]piperidine (E)-2-butenedioate (1:1) hydrate by thin layer chromatography.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customevaporated

Sources & evidence

ORD record
ord-2b1c1f2fe9e24c01ab08d21026a15d0d
Source dataset
uspto-grants-1981_02
Patent number
US04251655

Reaction notes

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