1,2-Dichloroethane → Pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride

HRID 1987854Notes

Reaction equation

HRID 1987854 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12].C(Cl)C[Cl:15].Cl.[N:18]12[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]1)[CH:20]([CH2:26][C:27](O)=[O:28])[CH2:19]2>C(N(CC)C(C)C)(C)C.ClCCl>[ClH:15].[N:18]12[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25]1)[CH:20]([CH2:26][C:27]([O:8][C:7]1[C:2]([F:1])=[C:3]([F:12])[C:4]([F:11])=[C:5]([F:10])[C:6]=1[F:9])=[O:28])[CH2:19]2

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 13041PentafluorophenolHCID 230241472-(Quinuclidin-3-yl)acetic acid hydrochloride

Product 1

HCID 86610796Pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride

Reagents, catalysts & solvents 2

HCID 81531DiisopropylethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

358 mg (1.94 mmol) of pentafluorophenol, 120.5 mg (0.63 mmol) of EDC and 1 drop of N,N-diisopropylethylamine are added to a solution of 100 mg (0.49 mmol) of 1-azabicyclo[2.2.2]oct-3-ylacetic acid hydrochloride in 4 ml of dichloromethane at 0° C. The mixture is stirred at room temperature for 18 h. The contents of the flask are concentrated in vacuo and dried under high vacuum. The resulting crude product is employed without further purification in the following stages.

Workup

  1. concentrationThe contents of the flask are concentrated in vacuo
  2. customdried under high vacuum
  3. customThe resulting crude product is employed without further purification in the following stages

Sources & evidence

ORD record
ord-6ecec183b4254164965029808230300a
Source dataset
uspto-grants-2009_06
Patent number
US07553851B2

Reaction notes

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