2-Piperidinoethyl isothiocyanate → 3-isobutyl-1-oxo-3-phenyl-N-(2-(piperidin-1-yl)ethyl)-3,4,6,7-tetrahydrofuro[3,4-c]pyridine-5(1H)-carbothioamide

HRID 1747741Notes

Reaction equation

HRID 1747741 reaction equation
[C:1]1([C:7]2([CH2:17][CH:18]([CH3:20])[CH3:19])[C:11]3[CH2:12][NH:13][CH2:14][CH2:15][C:10]=3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:21]([CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[C:22]=[S:23]>ClCCl>[CH2:17]([C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]2[CH2:12][N:13]([C:22](=[S:23])[NH:21][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:14][CH2:15][C:10]=2[C:9](=[O:16])[O:8]1)[CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 27604612-Piperidinoethyl isothiocyanateHCID 896147743-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one

Product 1

HCID 896158863-isobutyl-1-oxo-3-phenyl-N-(2-(piperidin-1-yl)ethyl)-3,4,6,7-tetrahydrofuro[3,4-c]pyridine-5(1H)-carbothioamideYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-phenyl-3-isobutyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (50 mg, 0.18 mmol) and 1-(isothiocyanatoethyl)piperidine (45.7 mg, 0.28 mmol) in dichloromethane (5 mL) was stirred at room temperature for 1 h. The solvent was removed and the resulting residue was purified on silica to give the desired product (52 mg, 64.0%). 1H NMR (300 Hz, CDCl3) δ 0.87 (t, J=6.0, 3H), 0.96 (t, d=6.0, 3H), 1.40-1.63 (m, 6H), 1.63-1.75 (m, 1H), 1.78-1.90 (m, 1H), 2.30-2.60 (m, 10H), 2.58-2.70 (m, 3H), 3.83-3.95 (m, 1H), 4.26 (d, J=18.0, 1H), 5.17 (d, J=18.0, 1H), 7.02 (br s, 1H), 7.26-7.40 (m, 5H).

Workup

  1. customThe solvent was removed
  2. customthe resulting residue was purified on silica

Sources & evidence

ORD record
ord-26f266c2731b4ae6a2161b98dacefc61
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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