1,4-Dibromobutane → N-[4-(1-Adamantyloxy)-3,5-dimethylphenyl]pyrrolidine

HRID 66097Notes

Reaction equation

HRID 66097 reaction equation
Cl.[C:2]12([O:12][C:13]3[C:19]([CH3:20])=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=3[CH3:21])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.[OH-].[Na+].Br[CH2:25][CH2:26][CH2:27][CH2:28]Br.C([O-])([O-])=O.[K+].[K+]>C(O)C.O>[C:2]12([O:12][C:13]3[C:14]([CH3:21])=[CH:15][C:16]([N:17]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:18][C:19]=3[CH3:20])[CH2:9][CH:8]3[CH2:7][CH:6]([CH2:5][CH:4]([CH2:10]3)[CH2:3]1)[CH2:11]2

Participants

7

Reactant 4

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 20342224HCID 20342224, compound

Product 1

HCID 12510314N-[4-(1-Adamantyloxy)-3,5-dimethylphenyl]pyrrolidine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The amine obtained by washing a CH2Cl2 solution of 2.1 g. (6.82 mmole) of 4-(1-adamantyloxy)-3,5-dimethylaniline hydrochloride with three 25 ml. portions of 10% aq. NaOH followed by a water wash, drying (anhydrous MgSO4) and concentration, was combined with 1.47 g. (6.82 mmole) of 1,4-dibromobutane and 2.07 g. (15.0 mmole) of K2CO3 in 20 ml. of absolute ethanol and refluxed for approximately 18 hours.

Workup

  1. washby washing a CH2Cl2 solution of 2.1 g
  2. washwash
  3. customdrying
  4. concentration(anhydrous MgSO4) and concentration

Sources & evidence

ORD record
ord-84f17fd872024601a2eeeb16e6fa15d6
Source dataset
uspto-grants-1978_12
Patent number
US04130561

Reaction notes

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