Hydrochloric Acid → 2-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(8-nitro-2-naphthyl)acetamide hydrochloride

HRID 55776Notes

Reaction equation

HRID 55776 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([CH2:10][C:11]([OH:13])=O)[CH2:3]2.S(Cl)([Cl:16])=O.C(N(CC)CC)C.[N+:25]([C:28]1[CH:29]=[CH:30][CH:31]=[C:32]2[C:37]=1[CH:36]=[C:35]([NH2:38])[CH:34]=[CH:33]2)([O-:27])=[O:26].Cl>CN(C=O)C.CN(C1C=CN=CC=1)C>[ClH:16].[N:2]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[CH:4]([CH2:10][C:11]([NH:38][C:35]1[CH:34]=[CH:33][C:32]3[C:37](=[C:28]([N+:25]([O-:27])=[O:26])[CH:29]=[CH:30][CH:31]=3)[CH:36]=1)=[O:13])[CH2:3]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 24386Thionyl Chloride2×HCID 6047078-Nitro-2-naphthalenamineHCID 230241472-(Quinuclidin-3-yl)acetic acid hydrochloride

Product 1

HCID 179798212-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(8-nitro-2-naphthyl)acetamide hydrochloride

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

200 mg (0.97 mmol) of 1-azabicyclo[2.2.2]oct-3-ylacetic acid hydrochloride are heated under reflux in 2 ml (27.42 mol) of thionyl chloride for 2 h. The mixture is then freed of excess thionyl chloride in vacuo, and the residue is taken up in 4 ml of DMF. 0.54 ml (3.89 mmol) of triethylamine, 59.4 mg (0.4 mmol) of DMAP and 183.0 mg (0.97 mmol) of 8-nitro-2-naphthylamine are added to this solution. After reaction overnight and purification by preparative HPLC, the resulting product fractions are mixed with 1 M hydrochloric acid and concentrated in vacuo. Recrystallization, of the residue from isopropanol and drying under high vacuum result in 59 mg (15% of theory) of the title compound.

Workup

  1. customAfter reaction overnight and purification by preparative HPLC
  2. concentrationconcentrated in vacuo
  3. customRecrystallization
  4. dry with materialof the residue from isopropanol and drying under high vacuum

Sources & evidence

ORD record
ord-6cec85f52d064144a707cce7c3bf4a26
Source dataset
uspto-grants-2016_09
Patent number
US09433614B2

Reaction notes

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