Diethyl Ether → HCID 13272327, compound

HRID 364639Notes

Reaction equation

HRID 364639 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][Cl:6].[NH2:10][CH:11]1[CH:16]2[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]2)[CH2:12]1.CC[O:21]CC>>[ClH:6].[N:13]12[CH2:18][CH2:17][CH:16]([CH2:15][CH2:14]1)[CH:11]([NH:10][C:5](=[O:21])[C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=1)[CH2:12]2

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 99743-Fluorobenzyl chlorideHCID 1232383-Aminoquinuclidine

Product 1

HCID 13272327HCID 13272327, compound

Procedure

In a closed system, a solution of 3-fluorobenzyl 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-a7848ca61f4a4fe8951a234bfc94fe5d
Source dataset
uspto-grants-1986_08
Patent number
US04605652

Reaction notes

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