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1-(2-Chloroethyl)pyrrolidine → 4-Adamantoyloxy-N-methyl-N-(2-pyrrolidinoethyl)aniline Dihydrochloride Dihydrate

HRID 66092
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HRID 66092 반응식
CNC1C=CC([O:9][C:10]23[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]4)[CH2:11]2)[CH2:17]3)=CC=1.[Cl:20]CCN1CCCC1.[OH2:28].O.[ClH:30].Cl.[C:32]12([O:42][C:43]3[CH:57]=[CH:56][C:46]([N:47]([CH3:55])[CH2:48][CH2:49][N:50]4[CH2:54][CH2:53][CH2:52][CH2:51]4)=[CH:45][CH:44]=3)CC3CC(CC(C3)C1)C2>CCCCC.C1C=CC=CC=1.C1COCC1.C1(C)C=CC=CC=1>[OH2:9].[OH2:42].[ClH:20].[ClH:30].[C:10]12([C:32]([O:42][C:43]3[CH:57]=[CH:56][C:46]([N:47]([CH3:55])[CH2:48][CH2:49][N:50]4[CH2:54][CH2:53][CH2:52][CH2:51]4)=[CH:45][CH:44]=3)=[O:28])[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 816691-(2-Chloroethyl)pyrrolidineHCID 12510299N-Methyl-p-(1-adamantyloxy)anilineHCID 203421994-adamantyloxy-N-methyl-N-(2-pyrrolidinoethyl)aniline dihydrochloride dihydrate

생성물 1

HCID 705880674-Adamantoyloxy-N-methyl-N-(2-pyrrolidinoethyl)aniline Dihydrochloride Dihydrate

시약·촉매·용매 4

HCID 241Benzene용매
HCID 1140
Toluene
용매
HCID 8003Pentane용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

To an ice-MeOH cooled solution of 2.0 g. (0.0078 mole) of N-Methyl-p-(1-adamantyloxy)aniline in 20 ml. THF was added 4.75 ml. of 1.64 N Buli in pentane. A solution of a 1:1 mixture of toluene, and 1-chloro-2-pyrrolidino ethane (2.08 g.) in 20 ml. THF was then added and the mixture stirred at room temperature for 1 hour and at reflux for 18 hours. The solution was allowed to cool, diluted with C6H6 and washed with H2O and brine. The residue remaining when the organic fraction was taken to dryness was dissolved in CH2Cl2, treated with 10 ml. HCl saturated Et2O and taken to dryness The residual solid was recrystallized from CH2Cl2 :CH3CN to yield 1.93 g. (55%) of 4-adamantyloxy-N-methyl-N-(2-pyrrolidinoethyl)aniline dihydrochloride dihydrate, m.p. 189°-190° (efervess).

후처리

  1. temperatureat reflux for 18 hours
  2. temperatureto cool
  3. washwashed with H2O and brine
  4. dissolutionwas dissolved in CH2Cl2
  5. additiontreated with 10 ml
  6. customwas recrystallized from CH2Cl2
  7. customCH3CN to yield 1.93 g

출처 및 근거

ORD 기록
ord-695e9d1956644d589e9cb00719323cba
출처 데이터셋
uspto-grants-1978_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04130561

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