1,4-Dibromobutane → [4-(1-Adamantyloxy)-2,6-dimethylphenyl]pyrrolidine

HRID 66101Notes

Reaction equation

HRID 66101 reaction equation
[C:1]12([O:11][C:12]3[CH:18]=[C:17]([CH3:19])[C:15]([NH2:16])=[C:14]([CH3:20])[CH:13]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Br[CH2:22][CH2:23][CH2:24][CH2:25]Br.C([O-])([O-])=O.[K+].[K+]>C(O)C>[C:1]12([O:11][C:12]3[CH:13]=[C:14]([CH3:20])[C:15]([N:16]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[C:17]([CH3:19])[CH:18]=3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 125102894-(1-Adamantyloxy)-2,6-dimethylaniline

Product 1

HCID 12510315[4-(1-Adamantyloxy)-2,6-dimethylphenyl]pyrrolidineYield 111.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.8 g (6.63 mmoles) of 4-(1-adamantyloxy)-2,6-dimethylaniline, 1.43 g (6.63 mmoles) of 1,4-dibromobutane, and 2.01 g (14.6 mmoles) of K2CO3 in 25 deaerated absolute ethanol is refluxed for 45 hours, cooled, and evaporated. The residue is taken up in CH2Cl2 (125 ml) and water (125 ml). The CH2Cl2 layer is washed with water, and the combined aqueous layers are extracted with CH2Cl2 (50 ml.). The combined organic layers are dried and concentrated to give 2.4 g of a brown oil, which is chromatographed by HPLC on a 2.54 cm×109 cm column at 40 psi eluting with 0.5% acetone in CH2Cl2 and then 0.75% acetone in CH2Cl2 to give 0.45 g in the first liter eluted from the column. This solid in 1 ml of CH2Cl2 and 5 ml of ether is treated with 3.5 N HCl in ether. The hydrochloride is filtered, washed with ether, and dried to give 0.38 g of white solid, m.p. 184.4-185.6 (dec.).

Workup

  1. temperatureis refluxed for 45 hours
  2. temperaturecooled
  3. customevaporated
  4. washThe CH2Cl2 layer is washed with water
  5. extractionthe combined aqueous layers are extracted with CH2Cl2 (50 ml.)
  6. customThe combined organic layers are dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8f4a6b6b5e684f1f9588a444fc2397d0
Source dataset
uspto-grants-1978_12
Patent number
US04130561

Reaction notes

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