Isopropylamine → 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-N-isopropylacetamide

HRID 517849Notes

Reaction equation

HRID 517849 reaction equation
[CH3:1][N:2]1[CH2:21][CH2:20][C:5]2[N:6]([CH2:14][C:15](OCC)=[O:16])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[CH:22]([NH2:25])([CH3:24])[CH3:23]>>[CH3:1][N:2]1[CH2:21][CH2:20][C:5]2[N:6]([CH2:14][C:15]([NH:25][CH:22]([CH3:24])[CH3:23])=[O:16])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 44158421Ethyl 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetate

Product 1

HCID 441594532-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-N-isopropylacetamide

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetate (100 mg) and isopropylamine (1 ml) was heated at 120° C. for 15 h to obtain 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-N-isopropylacetamide after purification on neutral alumina chromatography eluting with methanol-dichloromethane gradient. The free base was converted into its oxalate salt by treatment of oxalic acid (1 equiv) in anhydrous THF.

Sources & evidence

ORD record
ord-2056409510314f45aad435e64430021d
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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