Hydrochloric Acid → HCID 20393375, compound

HRID 1863077Notes

Reaction equation

HRID 1863077 reaction equation
CN.Cl.Cl.[CH2:5]([N:7]([CH2:30][CH3:31])[CH2:8][CH2:9][NH:10][C:11](=[O:29])[C:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[C:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O)[CH3:6].[C:32]([BH3-])#[N:33].[Na+]>CO>[ClH:20].[CH2:5]([N:7]([CH2:30][CH3:31])[CH2:8][CH2:9][NH:10][C:11]([C:12]1[N:33]([CH3:32])[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:15]2[C:14]=1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16]2)=[O:29])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 86736117HCID 86736117, compound

Product 1

HCID 20393375HCID 20393375, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7.45 g. of methylamine in 120 ml. of methanol is treated with 12 ml. of 6.65-N methanolic hydrochloric acid. Thereafter, there are successively added under an atmosphere of argon at 20°-25° C. 17.0 g. of o-benzoyl-p-chlorophenylglyoxylic acid [2-(diethylamino)ethyl]amide hydrochloride and 1.6 g. of sodium cyanoborohydride and the mixture is stirred at room temperature for an addition 2 hours. The mixture is made acidic with concentrated hydrochloric acid while cooling with ice, stirred at room temperature for an additional 0.5 hour and evaporated to dryness under reduced pressure. The residue is made alkaline with 2-N ammonium hydroxide with the addition of ice and extracted with diethyl ether. After drying over sodium sulfate, the extract is concentrated to dryness and the oily residue triturated with hexane to crystallize the product. The product is removed by filtration, dissolved in 30 ml. of methanol and the solution treated with excess ethereal hydrochloric acid. After dilution with diethyl ether to a ten-fold volume, the hydrochloride which crystallizes out is removed by filtration and washed with diethyl ether. Recrystallization from methanol/diethyl ether yields 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid [2-(diethylamino)ethyl]amide hydrochloride in the form of almost colorless crystals having a melting point of 211°-214° C. (decomposition).

Workup

  1. additionThereafter, there are successively added under an atmosphere of argon at 20°-25° C
  2. temperaturewhile cooling with ice
  3. customevaporated to dryness under reduced pressure
  4. additionwith the addition of ice
  5. extractionextracted with diethyl ether
  6. dry with materialAfter drying over sodium sulfate
  7. concentrationthe extract is concentrated to dryness
  8. customthe oily residue triturated with hexane
  9. customto crystallize the product
  10. customThe product is removed by filtration
  11. dissolutiondissolved in 30 ml
  12. additionof methanol and the solution treated with excess ethereal hydrochloric acid
  13. customAfter dilution with diethyl ether to a ten-fold volume, the hydrochloride which crystallizes out
  14. customis removed by filtration
  15. washwashed with diethyl ether
  16. customRecrystallization from methanol/diethyl ether

Sources & evidence

ORD record
ord-dc0408adaff44c5a88d4b15f7f9f8983
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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