Triethylamine → Benzamide, N-[2-(5-chloro-1H-indol-3-yl)ethyl]-3-(phenylmethyl)-

HRID 1777590Notes

Reaction equation

HRID 1777590 reaction equation
S(Cl)(Cl)=O.[CH2:5]([C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=O)[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]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([NH:34][CH2:33][CH2:32][C:26]1[C:25]2[C:29](=[CH:30][CH:31]=[C:23]([Cl:22])[CH:24]=2)[NH:28][CH:27]=1)=[O:17])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 41245533-Benzylbenzoic acid

Product 1

HCID 67974395Benzamide, N-[2-(5-chloro-1H-indol-3-yl)ethyl]-3-(phenylmethyl)-Yield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
65 °C

Procedure

Thionyl chloride (0.113 mL; 1.55 mmol) was added to a mixture of 3-benzylbenzoic acid (0.110 g; 0.518 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 (0.110 g; 0.466 mmol) and triethylamine (0.363 mL; 2.59 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 0.154 g (76%) of 3-benzyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)benzamide as a white solid.

Workup

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

Sources & evidence

ORD record
ord-a783a7cfd85c4f16b39656aeaa1204a5
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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