Hydrogen Bromide → HCID 18461101, compound

HRID 2303325Notes

Reaction equation

HRID 2303325 reaction equation
C(OC([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[CH2:10]2)=O)C.Br.[OH-].[Na+]>C(O)(=O)C>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:9]2[CH2:8][CH:7]3[NH:6][CH:11]([CH2:12][CH2:13]3)[CH2:10]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 22958906HCID 22958906, compound

Product 1

HCID 18461101HCID 18461101, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2 g of 3-(4-chloro-benzyl)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester, 20 mL of 48% HBr and 5 mL of acetic acid was heated to reflux for 2 h. After cooling in an ice bath, the solution was basified to pH 10 by addition of NaOH pellets, extracted with 3×100 mL of chloroform, and the combined extracts dried over MgSO4. Removal of solvents under reduced pressure gave 1.5 g of 2:1 exo:endo 3-(4-chloro-benzyl)-8-aza-bicyclo[3.2.1]octane as a thick oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. temperatureAfter cooling in an ice bath
  4. extractionextracted with 3×100 mL of chloroform
  5. dry with materialthe combined extracts dried over MgSO4
  6. customRemoval of solvents under reduced pressure
  7. customgave 1.5 g of 2:1 exo

Sources & evidence

ORD record
ord-02a86ed4146d4483a4f3faf39f090136
Source dataset
uspto-grants-2002_08
Patent number
US06432976B1

Reaction notes

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