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

HRID 1465994Notes

Reaction equation

HRID 1465994 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
  2. concentrationconcentrated in vacuo
  3. customRecrystallization of the residue from isopropanol
  4. customdrying under high vacuum

Sources & evidence

ORD record
ord-76a819cf55ac4c1a931868ee3a0d6a0c
Source dataset
uspto-grants-2015_04
Patent number
US09000008B2

Reaction notes

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