3-Pyridinemethanamine → HCID 15961237, compound

HRID 1980740Notes

Reaction equation

HRID 1980740 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.CO[C:35]1[C:39](OC)=[N:38][S:37](=[O:42])[N:36]=1.[NH2:43][CH2:44][C:45]1[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=1>CO>[N:47]1[CH:48]=[CH:49][CH:50]=[C:45]([CH2:44][NH:43][C:35]2[C:39]([NH:15][CH2:14][CH2:13][CH2:12][O:11][C:10]3[CH:16]=[CH:17][CH:18]=[C:8]([CH2:7][N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:9]=3)=[N:38][S:37](=[O:42])[N:36]=2)[CH:46]=1

Participants

6

Reactant 4

HCID 310183-PyridinemethanamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxide

Product 1

HCID 15961237HCID 15961237, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3-(3-piperidinomethylphenoxy)propylamine (from the dihydrochloride, 3.21 g; 10.0 mmoles) in 30 ml of methanol was added dropwise over a period of 60 minutes to a partial solution of 3,4-dimethoxy-1,2,5-thiadiazole 1-oxide (1.62 g; 10.0 mmoles) that had been cooled to 5°-7° in an ice-water bath. After 3 hours at ambient temperature, a solution of 3-aminomethylpyridine (1.14 g; 10.5 mmoles) in 10 ml of methanol was added and the solution was then stirred for 18 hours. The reaction mixture was evaporated under reduced pressure and the residue chromatographed by flash chromatography on 100 g of silica gel (230-400 mesh) using methylene chloride-methanol-ammonia. The appropriate fractions were combined, evaporated and triturated with acetonitrile to give 4.05 g of product. Recrystallization from isopropyl alcohol yielded the title compound, mp 139.5°-143°.

Workup

  1. temperaturehad been cooled to 5°-7° in an ice-water bath
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customthe residue chromatographed by flash chromatography on 100 g of silica gel (230-400 mesh)
  4. customevaporated
  5. customtriturated with acetonitrile

Sources & evidence

ORD record
ord-77e1ecfd6fd14a3a86d7ac7d3e936b35
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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