1,1'-Thiocarbonyldiimidazole → HCID 19597355, compound

HRID 611484Notes

Reaction equation

HRID 611484 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][NH2:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](N1C=CN=C1)(N1C=CN=C1)=[S:18]>CC#N>[N:16]([CH2:15][CH2:14][CH2:13][N:10]1[CH2:9][CH2:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][CH2:11]1)=[C:17]=[S:18]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 22725156HCID 22725156, compound

Product 1

HCID 19597355HCID 19597355, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-phenyl-1-piperidinepropanamine (Example 5 intermediate) (3.2 g, 14.7 mmol) and 1,1'-thiocarbonyldiimidazole (2.8 g, 15.7 mmol) in MeCN (100 mL) was stirred for 2 h. The reaction mixture was chromatographed by vacuum filtration over silica (MeCN) to furnish 1-(3-isothiocyanatopropyl)-4-phenylpiperidine as an amber oil which crystallized upon standing (1.25 g, 33%). mp 50-55° C.; MS (ESI) m/z 261 (MH+); IR (KBr) 2113 cm-1. 1H NMR (CDCl3) δ 7.23 (m, 5H), 3.63 (t, 2 H, J=6.3 Hz), 3.08 (m, 2H), 2.55 (t, 2H, J=7.2 Hz), 2.50 (m, 1H), 2.15 (m, 2H), 1.95 (t, 2H, J=6.9 Hz), 1.86 (m, 4H). Anal. Calcd. for C15H20N2S.0.5 C2H3N: C, 66.28; H, 7.82; N, 12.08. Found: C, 66.68; H, 7.75; N, 12.22.

Workup

  1. filtrationThe reaction mixture was chromatographed by vacuum filtration over silica (MeCN)

Sources & evidence

ORD record
ord-550db63b15f440b3a9133e16a54927c7
Source dataset
uspto-grants-1999_12
Patent number
US06001836

Reaction notes

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