Sodium triacetoxyborohydride → (3,5-Dimethyl-pyridin-2-ylmethyl)-(1-methyl-1-pyridin-2-yl-ethyl)-amine

HRID 251041Notes

Reaction equation

HRID 251041 reaction equation
[CH3:1][C:2]([NH2:10])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:3].[CH3:11][C:12]1[C:13]([CH:19]=O)=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:11][C:12]1[C:13]([CH2:19][NH:10][C:2]([CH3:3])([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=2)[CH3:1])=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 187316833,5-Dimethylpyridine-2-carbaldehydeHCID 227369222-(2-Pyridyl)-2-propylamine

Product 1

HCID 67272239(3,5-Dimethyl-pyridin-2-ylmethyl)-(1-methyl-1-pyridin-2-yl-ethyl)-amineYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of 1-methyl-1-pyridin-2-yl-ethylamine, 3,5-dimethylpyridine-2-carbaldehyde and NaBH(OAc)3 in CH2Cl2 gave (3,5-dimethyl-pyridin-2-ylmethyl)-(1-methyl-1-pyridin-2-yl-ethyl)-amine as a light brown oil (94 mg, 36%).

Sources & evidence

ORD record
ord-17dd2ef569e9431abbcc0bb54b139773
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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