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

HRID 2050209Notes

Reaction equation

HRID 2050209 reaction equation
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

Participants

10

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 5

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 1140TolueneSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fcb9e0995f07481c99b0d716c6297a28
Source dataset
uspto-grants-1980_04
Patent number
US04200588

Reaction notes

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