Hydrochloric Acid → (+/-)-4-[1-(6-Methoxypyridin-2-yl)-2,2-dipyridin-3-ylethyl]morpholine

HRID 1360123Notes

Reaction equation

HRID 1360123 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH:9]([NH2:23])[CH:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:6]=[CH:5][CH:4]=1.[O:24]([CH2:28][CH:29]=O)[CH2:25][CH:26]=O.O.[BH3-]C#N.[Na+].Cl>CC#N>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH:9]([N:23]2[CH2:29][CH2:28][O:24][CH2:25][CH2:26]2)[CH:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 819582,2'-OxybisacetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 574257591-(6-Methoxypyridin-2-yl)-2,2-dipyridin-3-ylethanamine

Product 1

HCID 59706156(+/-)-4-[1-(6-Methoxypyridin-2-yl)-2,2-dipyridin-3-ylethyl]morpholine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(6-methoxypyridin-2-yl)-2,2-dipyridin-3-ylethanamine (75 mg, 0.25 mmole) in CH3CN (1 mL) was added a solution of 2,2′-oxydiacetaldehyde in H2O (1.47 mL, 0.5 M, 0.73 mmole). After 10 minutes NaBH3CN (92 mg, 1.47 mmole) was added. After 2 hr 1N HCl (2 mL) was added.

Sources & evidence

ORD record
ord-07208786bb034bc78351ff260ad57854
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

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