Methylamine → HCID 53760783, compound

HRID 2226925Notes

Reaction equation

HRID 2226925 reaction equation
C([O:3][C:4]([CH:6]1[CH2:19][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=O)C.[CH3:20][NH2:21]>C(O)C>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]2[NH:10][C:9]3[CH2:19][CH:6]([C:4]([NH:21][CH3:20])=[O:3])[CH2:7][C:8]=3[C:16]=2[CH:15]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 53857755HCID 53857755, compound

Product 1

HCID 53760783HCID 53760783, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

1,2,3,4-tetrahydro-7-methoxycyclopent[b]indol-2-carboxylic acid ethyl ester (10.0 g, 0.039 mole) was added to a solution of methyl amine (6.0 g, 0.19 mole) and 40 ml of ethanol in a sealed tube. The mixture was heated to 100° C. and stirred for 96 hours. The mixture was concentrated to yield a brown solid (10.4 g), which was triturated with 50% ethyl acetate in CH2Cl2 to yield a tan solid (3.3 g). A portion (1.5 g) of this material was recrystallized from acetonitrile to yield 1.1 g of the product as a tan solid, m.p. 191°-193° C.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-c9d3cf2072394613ae36067765781eeb
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

Loading…