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Hydrochloric Acid → 4-{3-[4-(3-Hydroxypropyl)-1-piperidinyl]propoxy}benzonitrile monohydrate

HRID 43275
ノート
印刷プレビュー

反応式

HRID 43275 の反応式
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=1)(=O)=[O:3].[I-].[K+].C(=O)(O)[O-].[Na+].Cl.[NH:26]1[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33][CH2:34][OH:35])[CH2:28][CH2:27]1.Cl>CN(C)C=O.C1(C)C=CC=CC=1.O>[OH2:3].[OH:35][CH2:34][CH2:33][CH2:32][CH:29]1[CH2:30][CH2:31][N:26]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)[CH2:27][CH2:28]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 184257203-(Piperidin-4-yl)propan-1-ol hydrochlorideHCID 860892793-(4-Cyanophenoxy)propyl methanesulfonate

生成物 1

HCID 684343824-{3-[4-(3-Hydroxypropyl)-1-piperidinyl]propoxy}benzonitrile monohydrate収率 83.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

Into a solution of 50.0 g of 3-(4-cyanophenoxy)propyl methanesulfonate in 250 mL of N,N-dimethylformamide, 32.5 g of potassium iodide, 32.9 g of sodium bicarbonate and 37.0 g of 3-(4-piperidinyl)-1-propanol hydrochloride were added at room temperature, which was then stirred at 70° C. for 7 hours. To the reaction mixture, after being cooled down to room temperature, 250 mL of water and 150 mL of toluene were added, and then hydrochloric acid was added to adjust the pH to 1.0. The aqueous layer was separated, adjusted to pH 10.0 with a 20% sodium hydroxide aqueous solution, and stirred at room temperature for 15 min and under cooling on ice for 30 min. The solid matter was collected by filtration and washed twice with 50 mL of water and twice with 50 mL of toluene to obtain 52.3 g of 4-{3-[4-(3-hydroxypropyl)-1-piperidinyl]propoxy}benzonitrile monohydrate as a white solid.

後処理

  1. temperatureTo the reaction mixture, after being cooled down to room temperature
  2. customThe aqueous layer was separated
  3. stirringstirred at room temperature for 15 min
  4. temperatureunder cooling on ice for 30 min
  5. filtrationThe solid matter was collected by filtration
  6. washwashed twice with 50 mL of water and twice with 50 mL of toluene

出典と根拠

ORDレコード
ord-236e301dba894c7bb118600cfe5dbadb
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08536343B2

反応ノート

読み込み中…

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