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

HRID 251265Notes

Reaction equation

HRID 251265 reaction equation
[CH3:1][C:2]([NH2:10])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:3].[Cl:11][C:12]1[CH:13]=[C:14]([CH3:20])[C:15]([CH:18]=O)=[N:16][CH:17]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[C:14]([CH3:20])[C:15]([CH2:18][NH:10][C:2]([CH3:3])([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=2)[CH3:1])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 227369222-(2-Pyridyl)-2-propylamineHCID 722140555-Chloro-3-methylpicolinaldehyde

Product 1

HCID 67272856(5-Chloro-3-methyl-pyridin-2-ylmethyl)-(1-methyl-1-pyridin-2-yl-ethyl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of 1-methyl-1-pyridin-2-yl-ethylamine and 5-chloro-3-methyl-pyridine-2-carbaldehyde in CH2Cl2 with NaBH(OAc)3 gave (5-chloro-3-methyl-pyridin-2-ylmethyl)-(1-methyl-1-pyridin-2-yl-ethyl)-amine as a beige oil. 1H NMR (CDCl3) δ 1.61 (s, 6H), 2.19 (s, 3H), 3.62 (s, 2H), 4.66 (s, 1H), 7.11-7.15 (m, 1H), 7.38 (s, 1H), 7.48 (d, 1H, J=6.0 Hz), 7.62-7.67 (m, 1H), 8.37 (s, 1H), 8.58 (d, 1H, J=6.0 Hz).

Sources & evidence

ORD record
ord-e2cc72e094a34577a43c16bffb078698
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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