Dichloromethane → (3,5-Dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 251225Notes

Reaction equation

[CH3:1][C:2]1[C:3]([CH2:9][NH2:10])=[N:4][CH:5]=[C:6](C)[CH:7]=1.[N:11]1[C:20]2C(=O)CC[CH2:16][C:15]=2[CH:14]=[CH:13][CH:12]=1.[BH-](OC(C)=O)(OC(C)=O)O[C:24]([CH3:26])=O.[Na+].[CH2:36](Cl)Cl>>[CH3:16][C:15]1[C:20]([NH:10][CH:9]2[C:3]3[N:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH2:1][CH2:26][CH2:24]2)=[N:11][CH:12]=[C:13]([CH3:36])[CH:14]=1

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 5049666Sodium triacetoxyborohydride

HCID 117447776,7-Dihydro-5H-quinoline-8-one

HCID 18507412(3,5-Dimethylpyridin-2-yl)methanamine

Product 1

HCID 67273035(3,5-Dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

Procedure

Using General Procedure B, reaction of C-(3,5-dimethyl-pyridin-2-yl)-methylamine, 6,7-dihydro-5H-quinolin-8-one and NaBH(OAc)3 in CH2Cl2 gave (3,5-dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine as a light brown oil. 1H NMR (CDCl3) δ 1.76 (m, 1H), 1.92 (m, 1H), 2.06 (m, 1H), 2.19 (m, 1H), 2.26 (s, 3H), 2.33 (s, 3H), 2.80 (m, 2H), 3.88 (t, 1H, J=7.2 Hz), 3.96 (d, 1H, J=12.0 Hz), 4.10 (d, 1H, J=12.5 Hz), 7.04 (m, 1H), 7.23 (s, 1H), 7.35 (d, 1H, J=7.5 Hz), 8.23 (s, 1H), 8.41 (d, 1H, J=4.5 Hz).

Sources & evidence

ORD record: ord-97a19941bbad474c8d4e118a081ded33
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863293B2

Reaction notes

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