3-Aminoquinuclidine → HCID 68115053, compound

HRID 1606915Notes

Reaction equation

HRID 1606915 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:13]([Cl:15])=[O:14])=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[NH2:16][CH:17]1[CH:22]2[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]2)[CH2:18]1>C(Cl)Cl>[ClH:15].[N:19]12[CH2:24][CH2:23][CH:22]([CH2:21][CH2:20]1)[CH:17]([NH:16][C:13]([C:4]1[C:3]([O:2][CH3:1])=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=1)=[O:14])[CH2:18]2

Participants

4

Reactant 2

HCID 1232383-AminoquinuclidineHCID 603802HCID 603802, compound

Product 1

HCID 68115053HCID 68115053, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.69 g (0.00768 mole) of 3-methoxy-2-naphthoic acid chloride in 15 ml of methylene chloride was added dropwise to a stirred solution of 0.97 g (0.00768 mole) of 3-aminoquinuclidine in 25 ml of methylene chloride in a closed system equipped with an oil bubbler. The reaction mixture was stirred overnight at ambient temperature, and then concentrated to give an off-white glassy solid. Two recrystallizations from methanol-isopropyl ether gave 1.95 g (73.4%) of the product as an off-white solid which was vacuum dried at ambient temperature, m.p. 248°-252° C.

Workup

  1. customequipped with an oil bubbler
  2. concentrationconcentrated
  3. customto give an off-white glassy solid
  4. customTwo recrystallizations from methanol-isopropyl ether

Sources & evidence

ORD record
ord-abaf66432a93473a963905f957da7a32
Source dataset
uspto-grants-1989_09
Patent number
US04863919

Reaction notes

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