Triethylamine → HCID 178512293, compound

HRID 1383449Notes

Reaction equation

HRID 1383449 reaction equation
[C:1]([NH:3][C:4](=[N:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)SC)#[N:2].[CH:14]1[C:24]2[CH2:23][CH2:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[CH:19]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH2:35])[C:18]=2[CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>N1C=CC=CC=1.C(OCC)C>[CH:25]1[C:21]2[CH2:22][CH2:23][C:24]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[CH:19]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:4]([NH:3][C:1]#[N:2])=[N:7][C:8]3[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=3)[C:20]=2[CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 155219651-Cyano-2-methyl-3-pyridin-4-yl-isothioureaHCID 211877625-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yloxy)-pentylamine

Product 1

HCID 178512293HCID 178512293, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

1-Cyano-2-methyl-3-pyridin-4-yl-isothiourea (573 mg, 3.00 mmol) and 5-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yloxy)-pentylamine (886 mg, 3.00 mmol) were dissolved in pyridine (20 mL). Triethylamine (2 mL, 14 mmol) was added followed by (4-dimethylamino)pyridine (5.0 mg, 0.04 mmol). The reaction mixture was stirred at 86□ C. for 12 hours. After cooling to room temperature, the reaction mixture was diluted with diethyl ether (50 mL). The resulting precipitate was collected by filtration and washed with diethyl ether. The crude product was recrystalized from methanol and diethyl ether to give the desired product as a white crystalline solid (yield 85%). 1H NMR (CDCl3, ppm): 8.54 (dd, 2H), 7.41-7.12 (m, 10H), 5.29 (s, 1H), 3.56-3.41 (m, 4H), 3.32 (dd, 2H), 3.05-2.95 (m, 2H), 1.71-1.41 (m, 6H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with diethyl ether
  3. customThe crude product was recrystalized from methanol and diethyl ether

Sources & evidence

ORD record
ord-a00b398a02d0438cb7b8d745f9694f8e
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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