3-Fluorobenzoyl chloride → HCID 13272327, compound

HRID 1606922Notes

Reaction equation

HRID 1606922 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([Cl:7])=[O:6].[NH2:11][CH:12]1[CH:17]2[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]2)[CH2:13]1>CCOCC>[ClH:7].[N:14]12[CH2:19][CH2:18][CH:17]([CH2:16][CH2:15]1)[CH:12]([NH:11][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=1)[CH2:13]2

Participants

4

Reactant 2

HCID 743763-Fluorobenzoyl chlorideHCID 1232383-Aminoquinuclidine

Product 1

HCID 13272327HCID 13272327, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a closed system, a solution of 3-fluorobenzoyl chloride (7.93 g, 0.050 mole) in 30 ml ether was added dropwise to a stirred solution of 3-aminoquinuclidine (6.3 g, 0.050 mole) in 100 ml ether. After the addition was completed, the mixture was stirred at ambient temperature for 16 hr. The solid hydrochloride salt was collected under a nitrogen atmosphere and vacuum dried for 2 hr, to yield 13.11 g (92.1%). The salt was recrystallized from absolute ethanol-isopropyl ether to give 8.87 g of a white solid. The material was recrystallized from ethanol, and vacuum dried for 12 hr at 70° C., m.p. 257°-258° C.

Workup

  1. additionAfter the addition
  2. customThe solid hydrochloride salt was collected under a nitrogen atmosphere
  3. customvacuum dried for 2 hr
  4. customto yield 13.11 g (92.1%)
  5. customThe salt was recrystallized from absolute ethanol-isopropyl ether

Sources & evidence

ORD record
ord-a1f6423a2dab4cdca3c39102d487790a
Source dataset
uspto-grants-1989_09
Patent number
US04863919

Reaction notes

Loading…