Ammonia → 2-(1,2,3,4-Tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetamide

HRID 517859Notes

Reaction equation

HRID 517859 reaction equation
[CH3:1][N:2]1[CH2:21][CH2:20][C:5]2[N:6]([CH2:14][C:15]([O:17]CC)=O)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[NH3:22]>>[CH3:1][N:2]1[CH2:21][CH2:20][C:5]2[N:6]([CH2:14][C:15]([NH2:22])=[O:17])[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 222AmmoniaHCID 44158421Ethyl 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetate

Product 1

HCID 441600592-(1,2,3,4-Tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetamide

Procedure

Ethyl 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetate (0.5 g, 1.75 mmol) was taken in 4 ml aqueous ammonia and microwaved at 120° C. for 5 min using Initiator (Biotage Microwave). The solid product precipitated out after the reaction was filtered through Buchner funnel and washed with 10% sodium bicarbonate (10 ml×2) followed by demineralised water (10 ml×2) wash. Product was vacuum dried and was taken in 5 ml ethanolic HCl, stirred for 15 minutes, concentrated in vacuo to afford 13 mg of 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetamide as HCl salt. 1H NMR (DMSO) 10.2 (bs, 1H), 7.62 (s, 1H), 7.21-7.3 (m, 3H), 6.9 (d, 1H), 4.75 (s, 2H), 4.45-4.51 (m, 1H), 4.21-4.25 (m, 1H), 3.12-3.17 (m, 4H), 2.97 (s, 3H), 2.19 (s, 3H).

Workup

  1. custommicrowaved at 120° C. for 5 min
  2. customThe solid product precipitated out after the reaction
  3. filtrationwas filtered through Buchner funnel
  4. washwashed with 10% sodium bicarbonate (10 ml×2)
  5. washwash
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-220444ec094b4403b309b502c20728ab
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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