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

HRID 1112505
ノート
印刷プレビュー

反応式

HRID 1112505 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2b69b8383cf84f3698bc7d4a79e33945
出典データセット
uspto-grants-1978_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04122265

反応ノート

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