m-Anisoyl chloride → HCID 13272326, compound

HRID 1606921Notes

Reaction equation

HRID 1606921 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([Cl:8])=[O:7].[NH2:12][CH:13]1[CH:18]2[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]2)[CH2:14]1>CCOCC>[ClH:8].[N:15]12[CH2:20][CH2:19][CH:18]([CH2:17][CH2:16]1)[CH:13]([NH:12][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:14]2

Participants

4

Reactant 2

HCID 74374m-Anisoyl chlorideHCID 1232383-Aminoquinuclidine

Product 1

HCID 13272326HCID 13272326, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a closed system, a solution of 3-methoxybenzoyl chloride (7.18 g, 0.04206 mole) in 30 ml ether was added dropwise to a stirred solution of 3-aminoquinuclidine (5.30 g, 0.04206 mole) in 100 ml of ether. The reaction mixture was stirred at ambient temperature for 16 hr. The solid hydrochloride salt was collected under nitrogen and dried in vacuo at ambient temperature to give 11.12 g (87.1%) of the product. The material was recrystallized from absolute ethanol-isopropyl ether to give 7.69 g. The product was vacuum dried for 20 hr over refluxing ethanol, and then for 24 hr over refluxing isooctane; m.p. 214°-215° C.

Workup

  1. customThe solid hydrochloride salt was collected under nitrogen
  2. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-f7a57f2fccb2497f9d990f53cd42fac6
Source dataset
uspto-grants-1989_09
Patent number
US04863919

Reaction notes

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