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

HRID 43275
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인쇄 미리보기

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HRID 43275 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-236e301dba894c7bb118600cfe5dbadb
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08536343B2

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