Triethylamine → HCID 53835887, compound

HRID 1976739Notes

Reaction equation

NC1C=C2C(C=CN2)=CC=1.[CH3:11][NH:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[CH:18][N:19]2[CH3:22])=[CH:15][CH:14]=1.C(N(CC)CC)C.[CH2:30]([O:37][C:38](Cl)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:11][NH:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[CH:18][N:19]2[CH3:22])=[CH:15][CH:14]=1.[CH2:30]([O:37][C:38](=[O:39])[N:12]([CH3:11])[C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[CH:18][N:19]2[CH3:22])=[CH:15][CH:14]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-Methyl-(1-methyl-1H-indol-6-yl)-amine was prepared from 6-amino indole in a manner similar to that described in Example 1 a. c) Methyl-(1-methyl-1H-indol-6-yl)-amine (50 mg, 0.33 mmole) was dissolved in methylene chloride (2 mL) and cooled to 0° C. Triethylamine (55 μl, 0.39 mmole) was added followed by benzylchloroformate (52 μL, 0.39 mmnole). The reaction was stirred at room temperature for 1 hr. The reaction mixture was washed with 0.1 N hydrochloric acid and the organic was dried over magnesium sulfate, filtered and concentrated. The product was purified by column chromatography in 25% ethyl acetate/hexane to give methyl-(1-methyl-1H-indol-6-yl)-carbamic acid benzyl ester (67 mg, 73%).

Workup

washThe reaction mixture was washed with 0.1 N hydrochloric acid
dry with materialthe organic was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe product was purified by column chromatography in 25% ethyl acetate/hexane

Sources & evidence

ORD record: ord-53a284cbc8734610804a8894ce91769e
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06228877B1

Reaction notes

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