Benzoyl isothiocyanate → 1-Benzoyl-3-[1-(naphth-2-ylmethyl)piperid-4-yl]thiourea

HRID 1382444Notes

Reaction equation

HRID 1382444 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)[CH2:4][CH2:3]1.[C:19]([N:27]=[C:28]=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[C:19]([NH:27][C:28]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)[CH2:6][CH2:7]1)=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 111958234-Amino-1-(2-naphthyl)methylpiperidine

Product 1

HCID 129423461-Benzoyl-3-[1-(naphth-2-ylmethyl)piperid-4-yl]thiourea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Amino-1-(naphth-2-ylmethyl)piperidine (1.0 g, 0.0042 m) and benzoylisothiocyanate (0.69 g, 0.0042 m) in toluene (120 cm3) was stirred at room temperature for 6 hours. The solvent was evaporated and the gum dissolved in isopropyl alcohol and acidified with ethanolic HCl. The solvent was evaporated and the residue dissolved in ethyl acetate. The title compound crystallised and was filtered and dried as the monohydrochloride quarterhydrate salt, m.p. 212°-214° C.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe gum dissolved in isopropyl alcohol
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. customThe title compound crystallised
  6. filtrationwas filtered
  7. dry with materialdried as the monohydrochloride quarterhydrate salt, m.p. 212°-214° C.

Sources & evidence

ORD record
ord-39a3d131d448413b9eec206ca86cb410
Source dataset
uspto-grants-1989_02
Patent number
US04806552

Reaction notes

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