Triethylamine → HCID 67974521, compound

HRID 1777591Notes

Reaction equation

S(Cl)(Cl)=O.[CH2:5]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[Cl:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][CH:27]=[C:26]2[CH2:32][CH2:33][NH2:34].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:5]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([NH:34][CH2:33][CH2:32][C:26]2[C:25]3[C:29](=[CH:30][CH:31]=[C:23]([Cl:22])[CH:24]=3)[NH:28][CH:27]=2)=[O:18])=[CH:19][CH:20]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Thionyl chloride (0.111 mL; 1.52 mmol) was added to a mixture of 4-benzylbenzoic acid (0.100 g; 0.508 mmol) in chloroform (10 mL). The reaction mixture was stirred at 65° C. for 18 hours and evaporated to dryness. The resulting residue was dissolved in chloroform (6 mL) and the solution is cooled to 0° C. A solution of 2-(5-Chloro-1H-indol-3-yl)ethanamine hydrochloride (0.108 g; 0.457 mmol) and triethylamine (0.357 mL; 2.54 mmol) in chloroform (6 ml) was then added and the mixture was stirred for 30 minutes at room temperature. The volatiles were removed under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 1 to 20% ethyl acetate in dichloromethane) to furnish 0.155 g (78%) of 4-benzyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)benzamide as a white solid.

Workup

customevaporated to dryness
dissolutionThe resulting residue was dissolved in chloroform (6 mL)
temperaturethe solution is cooled to 0° C
stirringthe mixture was stirred for 30 minutes at room temperature
customThe volatiles were removed under reduced pressure
customthe crude material was purified by flash chromatography on silica gel (eluent 1 to 20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record: ord-7c232467888d414d92b865a567cb8436
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266832B2

Reaction notes

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