Acetic Acid → HCID 69017074, compound

HRID 1455075Notes

Reaction equation

HRID 1455075 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[O:15][CH:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH2:12]3)=[N:6][CH:7]=1.C=O.[C:27]([BH3-])#[N:28].[Na+].[C:31](O)(=O)C>C(#N)C>[CH3:31][N:28]([CH3:27])[C:2]1[CH:7]=[N:6][C:5]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[O:15][CH:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH2:12]3)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridine

Product 1

HCID 69017074HCID 69017074, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Amino-2-(2-phenylchroman-6-yloxy)pyridine (ORM-10543) (0.20 g, 0.63 mmol) and 37% formaldehyde (0.73 ml, 0.80 mmol) were dissolved in acetonitrile (12 ml). Sodiumcyanoborohydride (0.16 g, 2.51 mmol) was added and the mixture was stirred for 30 minutes at the room temperature. The pH was adjusted to 6-7 with acetic acid and the reaction mixture was stirred additional 30 minutes. The solvent was evaporated. The residue was solvated to 10% potassiumhydroxide solution and extracted with methylene chloride. Organic phase was dried and evaporated. Recrystallization from diethylether yielded dimethyl-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]-amine in 92% purity. Recrystallization filtrate was evaporated. The residue was solvated in methylene chloride and 1M HCl-diethylether was added. Dimethyl-[2-(2-phenylchroman-6-yloxy)-pyridin-4-yl]-amine precipitated as a hydrochloride in 95.3% purity.

Workup

  1. stirringthe reaction mixture was stirred additional 30 minutes
  2. customThe solvent was evaporated
  3. extractionextracted with methylene chloride
  4. customOrganic phase was dried
  5. customevaporated
  6. customRecrystallization from diethylether

Sources & evidence

ORD record
ord-48e69de387fb428bacfefa40f957877a
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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