Potassium Carbonate → HCID 24833999, compound

HRID 2413714Notes

Reaction equation

HRID 2413714 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]2[C:9]=1[N:10]=[C:11]1[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]1.[CH:17]([N:20]([CH:23](C)C)[CH2:21]C)(C)[CH3:18].Cl.ClCCN(C)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[CH3:21][N:20]([CH2:17][CH2:18][N:5]1[CH2:6][CH2:7][C:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[NH:10][C:9]=2[CH:3]([CH2:2][OH:1])[CH2:4]1)[CH3:23]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 20155350HCID 20155350, compound

Product 1

HCID 24833999HCID 24833999, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of 7 g (0.0324 mol) of 5-hydroxymethylazepino[4,5-b]indole, of 10.04 g (0.0777 mol) of diisopropylethylamine, and of 5.6 g (0.0388 mol) of 1-chloro-2-dimethylaminoethane hydrochloride in 150 ml of chloroform is heated under reflux for 15 hours. The reaction mixture is then drowned in water and alkalified with a saturated aqueous solution of potassium carbonate. The organic phase is separated off and the aqueous phase is again extracted twice with 100 ml portions of chloroform. The organic phases are combined, washed with water, dried over magnesium sulphate, filtered and evaporated to dryness under vacuum. The residue is crystallized from ethyl acetate and yields 8.1 g of product.

Workup

  1. temperatureunder reflux for 15 hours
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is again extracted twice with 100 ml portions of chloroform
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness under vacuum
  8. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-ea10c92cd7c84cd28b4c17a6511cfa3c
Source dataset
uspto-grants-1988_01
Patent number
US04719208

Reaction notes

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