Diethylaminoethyl chloride → HCID 20393375, compound

HRID 1863081Notes

Reaction equation

HRID 1863081 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[C:5]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:6]([CH3:14])[C:7]=2[C:11]([NH2:13])=[O:12])[CH:3]=1.[CH2:21]([N:23]([CH2:26][CH2:27]Cl)[CH2:24][CH3:25])[CH3:22]>>[ClH:1].[CH2:21]([N:23]([CH2:26][CH3:27])[CH2:24][CH2:25][NH:13][C:11]([C:7]1[N:6]([CH3:14])[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:4]2[C:8]=1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3]2)=[O:12])[CH3:22]

Participants

3

Reactant 2

HCID 13364Diethylaminoethyl chlorideHCID 54488893HCID 54488893, compound

Product 1

HCID 20393375HCID 20393375, compound

Procedure

In accordance with the procedure described in Example 2, 2.85 g. of 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid amide are reacted with 0.02 mol. of diethylaminoethyl chloride. The methylene chloride extract containing the free base is concentrated to dryness and the pasty residue chromatographed on 300 g. of aluminum oxide (neutral, Brockmann, activity I) using methylene chloride/ethyl acetate (4:1) for the elution. The homogeneous fractions are combined and evaporated. The residual solid residue is dissolved in 10 ml. of acetone and treated with excess ethereal hydrochloric acid. The hydrochloride which crystallizes out is removed by filtration and washed with diethyl ether, whereby there is obtained 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid[2-(diethylamino)ethyl]amide hydrochloride having a melting point of 211°-214° C. (decomposition).

Workup

  1. extractionThe methylene chloride extract
  2. additioncontaining the free base
  3. concentrationis concentrated to dryness
  4. customthe pasty residue chromatographed on 300 g
  5. washfor the elution
  6. customevaporated
  7. dissolutionThe residual solid residue is dissolved in 10 ml
  8. additionof acetone and treated with excess ethereal hydrochloric acid
  9. customThe hydrochloride which crystallizes out
  10. customis removed by filtration
  11. washwashed with diethyl ether

Sources & evidence

ORD record
ord-93a45665172246888f8dc488c7878b88
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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