4-Aminopyridine → 4-Amino-1-[4-(1,3-diphenyl-1-propoxy)benzyl]pyridinium bromide

HRID 363018Notes

Reaction equation

HRID 363018 reaction equation
[C:1]1([CH:7]([O:16][C:17]2[CH:24]=[CH:23][C:20]([CH2:21][Br:22])=[CH:19][CH:18]=2)[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1>C(#N)C>[Br-:22].[NH2:25][C:26]1[CH:31]=[CH:30][N+:29]([CH2:21][C:20]2[CH:23]=[CH:24][C:17]([O:16][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:18][CH:19]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 17274-AminopyridineHCID 538499334-(1,3-Diphenyl-1-propoxy)benzyl bromide

Product 1

HCID 700538334-Amino-1-[4-(1,3-diphenyl-1-propoxy)benzyl]pyridinium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(1,3-diphenyl-1-propoxy)benzyl bromide 6-6 (0.381 g, 1.0 mmol) in acetonitrile (7 ml) was added 4-aminopyridine (6-7) (94 mg, 1.0 mmol) with stirring at room temperature. The mixture was stirred for 3 hrs and the resulting white suspension was filtered. The white solid obtained 6-8, melted at 215°-216.5° C. Recrystallization from acetonitrile raised the melting point to 218.5°-220° C.

Workup

  1. stirringThe mixture was stirred for 3 hrs
  2. filtrationthe resulting white suspension was filtered
  3. customThe white solid obtained 6-8, melted at 215°-216.5° C
  4. customRecrystallization from acetonitrile
  5. temperatureraised the melting point to 218.5°-220° C.

Sources & evidence

ORD record
ord-dc40cab9b43344ce9424f3baf3290470
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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