Acetonitrile → 4-[hydroxy(diphenyl)methyl]-1-(tetrahydro-2H-pyran-2-ylmethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 533790Notes

Reaction equation

HRID 533790 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[OH:10])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[Br:23]C[CH:25]1[CH2:30][CH2:29][CH2:28][O:27][CH2:26]1.[CH3:31]C#N>>[Br-:23].[OH:10][C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:4]12[CH2:5][CH2:6][N+:1]([CH2:31][CH:26]3[CH2:25][CH2:30][CH2:29][CH2:28][O:27]3)([CH2:2][CH2:3]1)[CH2:8][CH2:7]2

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 226172573-(Bromomethyl)oxaneHCID 239923851-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol

Product 1

HCID 689606574-[hydroxy(diphenyl)methyl]-1-(tetrahydro-2H-pyran-2-ylmethyl)-1-azoniabicyclo[2.2.2]octane bromideYield 50.8%

Procedure

Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0677 g, 0.231 mmol) and 3-(bromomethyl)tetrahydro-2H-pyran (0.050 mL, 0.390 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0508 g, 50.8%). EI-MS m/z 392(M+) Rt (1.84 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-221e365f36e44231942deb2075cdca6d
Source dataset
uspto-grants-2014_10
Patent number
US08853404B2

Reaction notes

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