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

HRID 259358

반응식

HRID 259358 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.[Li]CCCC.[Cl:25]CCN1CCCC1.[OH2:33].O.[ClH:35].Cl.[C:37]12([O:47][C:48]3[CH:62]=[CH:61][C:51]([N:52]([CH3:60])[CH2:53][CH2:54][N:55]4[CH2:59][CH2:58][CH2:57][CH2:56]4)=[CH:50][CH:49]=3)CC3CC(CC(C3)C1)C2>CCCCC.C1C=CC=CC=1.C1COCC1.C1(C)C=CC=CC=1.CO>[OH2:9].[OH2:47].[ClH:25].[ClH:35].[C:10]12([C:37]([O:47][C:48]3[CH:62]=[CH:61][C:51]([N:52]([CH3:60])[CH2:53][CH2:54][N:55]4[CH2:59][CH2:58][CH2:57][CH2:56]4)=[CH:50][CH:49]=3)=[O:33])[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2

참가 물질

10

반응물 4

HCID 816691-(2-Chloroethyl)pyrrolidineHCID 12510299N-Methyl-p-(1-adamantyloxy)anilineHCID 203421994-adamantyloxy-N-methyl-N-(2-pyrrolidinoethyl)aniline dihydrochloride dihydrateHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 5

HCID 241Benzene용매HCID 887Methanol용매HCID 1140Toluene용매HCID 8003Pentane용매HCID 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 1.64N 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. customThe residual solid was recrystallized from CH2Cl2
  7. customCH3CN to yield 1.93 g

출처 및 근거

ORD 기록
ord-77d61c5ff56a4c22b27a5758b6298f8a
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04036977

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