Dimethylamine → HCID 18963992, compound

HRID 2226920Notes

Reaction equation

HRID 2226920 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:5])C.CNC>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]([OH:5])=[O:3])[CH2:7][C:8]=3[C:16]=2[CH:15]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 53735277HCID 53735277, compound

Product 1

HCID 18963992HCID 18963992, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1,2,3,4-tetrahydro-7-methoxy-4-methylcyclopent[b]indole-2-carboxylic acid ethyl ester (6.2 g, 0.023 mole) in 25 ml of ethanol, was added dimethylamine (40% aqueous solution, 10 ml, 0.09 mole). After stirring at 100° C. in a sealed tube for four days, the solution was concentrated to a brown oil (~6 g), which was eluted on a silica gel column with 20% methanol/ethyl acetate via HPLC. The desired fraction was concentrated to a tan solid, 5.0 g, m.p. 162°-164° C.

Workup

  1. concentrationthe solution was concentrated to a brown oil (~6 g), which
  2. washwas eluted on a silica gel column with 20% methanol/ethyl acetate via HPLC
  3. concentrationThe desired fraction was concentrated to a tan solid, 5.0 g, m.p. 162°-164° C.

Sources & evidence

ORD record
ord-921277115dae4fb8958e8dd8b5dc2b04
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

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