Dichloromethane → HCID 14752993, compound

HRID 358736Notes

Reaction equation

HRID 358736 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(Cl)Cl.[C:14](Cl)(=[O:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>C(N(CC)CC)C>[C:14]([NH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1)(=[O:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67340Hexanoyl chlorideHCID 2560966-Aminoindole

Product 1

HCID 14752993HCID 14752993, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 4.24 g. 6-aminoindole in 300 ml. methylene chloride was stirred at 0° C. and 5.4 ml triethylamine followed by 4.2 ml. hexanoyl chloride was then added. The dark mixture was stirred for 1 hour and then filtered to remove a white precipitate. The filtrate was diluted with methylene chloride; washed sequentially with 10% w/v sodium hydrogen sulphate water, and brine; dried (MgSO4); and evaporated. The residue was crystallized from ethyl acetate and hexane to give 6-hexanamidoindole (E) as a white solid. Partial evaporation of the mother liquor gave a second crop of solid giving a combined yield of 4.5 g. (65%); NMR: 0.9 (t, 3H, CH3), 1.4 (m, 4H, CH3CH2CH2), 1.8 (m, 2H, CO.CH2CH2), 2.4 (t, 2H, CO.CH2), 6.5 (m, 1H, H3), 6.8 (dd, 1H, H 5), 7.2 (m, 2H, CO.NH+H2), 7.5 (d, 1H, H4), 8.1 (bs, 1H, H7), 8.3 (br, 1H, NH).

Workup

  1. filtrationfiltered
  2. customto remove a white precipitate
  3. additionThe filtrate was diluted with methylene chloride
  4. washwashed sequentially with 10% w/v sodium hydrogen sulphate water, and brine
  5. dry with materialdried (MgSO4)
  6. customand evaporated
  7. customThe residue was crystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-9210726fcd9f4190990f91ad8c2deb8e
Source dataset
uspto-grants-1991_03
Patent number
US04997844

Reaction notes

Loading…