Methylamine → 1,2,3,4-Tetrahydro-7-phenylmethoxy-N,4-dimethylcyclopent[b]indole-2-carboxylic acid amide

HRID 2226927Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH2:26][C:9]2[N:10]([CH3:25])[C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=O)C.[CH3:27][NH2:28]>C(O)C>[C:19]1([CH2:18][O:17][C:14]2[CH:13]=[CH:12][C:11]3[N:10]([CH3:25])[C:9]4[CH2:26][CH:6]([C:4]([NH:28][CH3:27])=[O:3])[CH2:7][C:8]=4[C:16]=3[CH:15]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In a 50 ml sealed tube, was added a solution of 1,2,3,4-tetrahydro-7-phenylmethoxy-4-methylcyclopent[b]indole-2-carboxylic acid ethyl ester (10 g, 0.03 mole) in 25 ml absolute ethanol, followed by methylamine (40% aqueous solution, 10 ml, 0.13 mole). After stirring at 100° C. for six days, the mixture was cooled. A tan solid precipitated, which was collected and dried to give 7.0 g of the product as a solid, m.p. 176°-177° C. A sample of this solid was recrystallized from ethanol/ether (1:1) to give white crystals, m.p. 181°-182° C.

Workup

customIn a 50 ml sealed tube
temperaturethe mixture was cooled
customA tan solid precipitated
customwhich was collected
customdried

Sources & evidence

ORD record: ord-ace5bbd3511947eabdeec9bfe17ced42
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05350762

Reaction notes

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