Methylamine → HCID 54541909, compound

HRID 2226926Notes

Reaction equation

HRID 2226926 reaction equation
C([O:3][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)C.[CH3:21][NH2:22]>C(O)C>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]2[N:10]([CH3:19])[C:9]3[CH2:20][CH:6]([C:4]([NH:22][CH3:21])=[O:3])[CH2:7][C:8]=3[C:16]=2[CH:15]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 53735277HCID 53735277, compound

Product 1

HCID 54541909HCID 54541909, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1,2,3,4-tetrahydro-4-methyl-7-methoxycyclopent[b]indole-2-carboxylic acid ethyl ester (4.5 g, 0.016 mole) in 100 ml of absolute ethanol, was added methylamine (40% aqueous solution, 15 ml, 6 g, 0.18 mole). The mixture was stirred at 70° C. for 50 hours in a sealed tube. The mixture was concentrated to a brown solid (~5 g) which was eluted on a silica gel column with ethyl acetate/dichloromethane (1:1) via HPLC. The desired fractions were combined and concentrated to a white solid, 3.0 g, mp 164°-165° C. A sample of this material was recrystallized from ethanol to afford the product as a white solid, mp 166°-167° C.

Workup

  1. concentrationThe mixture was concentrated to a brown solid (~5 g) which
  2. washwas eluted on a silica gel column with ethyl acetate/dichloromethane (1:1) via HPLC
  3. concentrationconcentrated to a white solid, 3.0 g, mp 164°-165° C
  4. customA sample of this material was recrystallized from ethanol

Sources & evidence

ORD record
ord-958f91c29cf0446f90a700984001f649
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

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