Triethylamine → HCID 19853873, compound

HRID 1650401Notes

Reaction equation

HRID 1650401 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[O:20][CH3:21])[C:4]=1[C:22]([OH:24])=O.C(N(CC)CC)C.S(Cl)(Cl)=O.[CH2:36]([N:38]([CH2:41][CH:42]([OH:45])[CH2:43][NH2:44])[CH2:39][CH3:40])[CH3:37]>C(Cl)Cl>[CH2:36]([N:38]([CH2:41][CH:42]([OH:45])[CH2:43][NH:44][C:22]([C:4]1[N:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[O:20][CH3:21])[C:6]2[C:11]([C:3]=1[O:2][CH3:1])=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:24])[CH2:39][CH3:40])[CH3:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 977491-Amino-3-(diethylamino)propan-2-olHCID 19853869HCID 19853869, compound

Product 1

HCID 19853873HCID 19853873, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

16.8 g of 3-methoxy-1-(2',4'-dimethoxyphenyl)-indole-2-carboxylic acid and 7 ml of triethylamine are dissolved in 50 ml of methylene chloride and the solution is added dropwise to 4 ml of thionyl chloride in 5 ml of methylene chloride. 8 g of 3-(N,N-diethylamino)-2-hydroxypropylamine dissolved in 10 ml of methylene chloride are added dropwise to this solution. The solution is poured into ice-water, the mixture is extracted with methylene chloride and the organic phase is washed with water, dried and evaporated. The 2-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-methoxy-1-(2', 4'-dimethoxyphenyl)-indole which remains is dissolved in isopropanol, and gaseous hydrogen chloride is added to the solution, whereupon the hydrochloride of the title compound crystallises out. Yield: 13.4 g, melting point: 166°-168° C.

Workup

  1. additionare added dropwise to this solution
  2. extractionthe mixture is extracted with methylene chloride
  3. washthe organic phase is washed with water
  4. customdried
  5. customevaporated
  6. dissolutionThe 2-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-methoxy-1-(2', 4'-dimethoxyphenyl)-indole which remains is dissolved in isopropanol
  7. additiongaseous hydrogen chloride is added to the solution, whereupon the hydrochloride of the title compound
  8. customcrystallises out

Sources & evidence

ORD record
ord-ecde85cf2dd04579bb85b226b8a47691
Source dataset
uspto-grants-1990_05
Patent number
US04924004

Reaction notes

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