Hydrochloric Acid → 5-Chloro-2-methyl-3-phenylisoindole-1-carboxylic acid [4-(isopropylamino)pentyl]amide hydrochloride

HRID 1863088Notes

Reaction equation

HRID 1863088 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].Cl.O=[C:7]([CH3:31])[CH2:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[N:15]([CH3:30])[C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:17]2[C:22]=1[CH:21]=[CH:20][C:19]([Cl:23])=[CH:18]2)=[O:13].C([BH3-])#N.[Na+]>CO>[ClH:23].[CH:1]([NH:4][CH:7]([CH3:31])[CH2:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[N:15]([CH3:30])[C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:17]2[C:22]=1[CH:21]=[CH:20][C:19]([Cl:23])=[CH:18]2)=[O:13])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6363IsopropylamineHCID 5003444Sodium cyanoborohydrideHCID 203933715-Chloro-2-methyl-3-phenylisoindole-1-carboxylic acid (4-oxopentyl)amide

Product 1

HCID 203933395-Chloro-2-methyl-3-phenylisoindole-1-carboxylic acid [4-(isopropylamino)pentyl]amide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5.2 ml. of isopropylamine in 25 ml. of methanol is treated with 4 ml. of 5-N methanolic hydrochloric acid. Thereafter, there are successively added under an atmosphere of argon at 20°-25° C. 3.7 g. of 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid(4-oxopentyl)amide and 0.4 g. of sodium cyanoborohydride and the mixture is then stirred at room temperature for 48 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 then concentrated to dryness under reduced pressure. The residue is made alkaline with 0.5-N sodium hydroxide with the addition of ice and extracted with 200 ml. of diethyl ether. The extract, dried over sodium sulfate, is concentrated to dryness and the residual oily base crystallized from hot hexane. The thus-obtained colorless base, which melts at 102°-105° C. is dissolved in 30 ml. of acetone and treated with excess ethereal hydrochloric acid. The separated hydrochloride is removed by filtration and washed with acetone, and there is obtained 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid [4-(isopropylamino)pentyl]amide hydrochloride in the form of colorless crystals having a melting point of 216°-218° C. (decomposition). Recrystallization from acetone/methanol does not increase the melting point.

Workup

  1. additionThereafter, there are successively added under an atmosphere of argon at 20°-25° C
  2. temperaturewhile cooling with ice
  3. concentrationconcentrated to dryness under reduced pressure
  4. additionwith the addition of ice
  5. extractionextracted with 200 ml
  6. dry with materialThe extract, dried over sodium sulfate
  7. concentrationis concentrated to dryness
  8. customthe residual oily base crystallized from hot hexane
  9. dissolutionThe thus-obtained colorless base, which melts at 102°-105° C. is dissolved in 30 ml
  10. additionof acetone and treated with excess ethereal hydrochloric acid
  11. customThe separated hydrochloride is removed by filtration
  12. washwashed with acetone

Sources & evidence

ORD record
ord-0cdb5d65f00f4c7386d94b684368adcf
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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