2,6-Dimethoxybenzoyl chloride → HCID 13272339, compound

HRID 364636Notes

Reaction equation

HRID 364636 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5]([Cl:7])=[O:6].[NH2:14][CH:15]1[CH:20]2[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]2)[CH2:16]1>C(OCC)C>[ClH:7].[N:17]12[CH2:22][CH2:21][CH:20]([CH2:19][CH2:18]1)[CH:15]([NH:14][C:5](=[O:6])[C:4]1[C:3]([O:2][CH3:1])=[CH:11][CH:10]=[CH:9][C:8]=1[O:12][CH3:13])[CH2:16]2

Participants

4

Reactant 2

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 1232383-Aminoquinuclidine

Product 1

HCID 13272339HCID 13272339, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a closed system equipped with an oil bubbler, a solution of 2,6-dimethoxybenzoyl chloride (1.89 g, 0.0095 mole) in 20 ml diethyl ether was added dropwise to a stirred solution of 3-aminoquinuclidine (1.26 g, 0.010 mole) in 50 ml of diethyl ether. After the addition was completed, the reaction mixture was stirred for 15 min, and the precipitate that had formed was filtered under nitrogen. The wet (hygroscopic) solid was immediately recrystallized from methanol-isopropyl ether to give 1.85 g (60%) of the product. The material was vacuum dried for 4 hr at 98° C., m.p. 266°-268° C.

Workup

  1. customIn a closed system equipped with an oil bubbler
  2. additionAfter the addition
  3. customthe precipitate that had formed
  4. filtrationwas filtered under nitrogen
  5. customThe wet (hygroscopic) solid was immediately recrystallized from methanol-isopropyl ether

Sources & evidence

ORD record
ord-2f4f8eee41674a23bb52d439f3375710
Source dataset
uspto-grants-1986_08
Patent number
US04605652

Reaction notes

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