Ethylamine → HCID 54335949, compound

HRID 2226928Notes

Reaction equation

HRID 2226928 reaction equation
C(O[C:4]([CH:6]1[CH2:20][C:9]2[N:10]([CH3:19])[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:5])C.[CH2:21]([NH2:23])[CH3:22]>C(O)C>[CH3:19][N:10]1[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][C:16]=2[C:8]2[CH2:7][CH:6]([C:4]([NH:23][CH2:21][CH3:22])=[O:5])[CH2:20][C:9]1=2

Participants

4

Reactant 2

HCID 6341EthylamineHCID 53735277HCID 53735277, compound

Product 1

HCID 54335949HCID 54335949, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

In a 50 ml sealed tube was dissolved 1,2,3,4-tetrahydro-4-methyl-7-methoxycyclopent[b]indole-2-carboxylic acid ethyl ester (2.8 g, 0.01 mole)in 25 ml of ethanol. To this was added an aqueous solution of ethylamine (70% solution, 5 ml, 0.075 mole). After stirring at 90° C. for five days, the mixture was concentrated to a brown solid, (~3 g) which was eluted on a silica gel column with ethyl acetate/dichloromethane (1:2) via HPLC. The desired fractions were combined to yield 1.3 g of a white solid, m.p. 162°-3° C. A sample of this material (0.5 g) was recrystallized from ethyl acetate/ether (1:10) to give the product as white crystals, 0.4 g, m.p. 163°-4° C.

Workup

  1. customIn a 50 ml sealed tube
  2. concentrationthe mixture was concentrated to a brown solid, (~3 g) which
  3. washwas eluted on a silica gel column with ethyl acetate/dichloromethane (1:2) via HPLC

Sources & evidence

ORD record
ord-8899d8b5e418470db1118d1c8dad1174
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

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