(+-)-Anabasine → Ammonia dichloromethane

HRID 33710Notes

Reaction equation

HRID 33710 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[CH2:47]([Cl:49])[Cl:48]>C(O)(=O)C>[NH3:1].[CH2:47]([Cl:49])[Cl:48].[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH2:15][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]3[C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 2181(+-)-AnabasineHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 102006161-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-1,2,3,4,5,6-hexahydro-[2,3']bipyridinylHCID 22731429Ammonia dichloromethaneYield 1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of Example 9 (174 mg), 1,2,3,4,5,6-hexahydro-[2,3′]bipyridinyl (111 mg), and acetic acid (0.05 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (240 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (5 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1-5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (112 mg). 1H NMR (400 MHz, CDCl3): 8.63 (m, 1H), 8.49 (m, 1H), 7.80 (m, 1H), 7.27 (m, 1H), 7.11 (d, J=8.6 Hz, 2H) 6.80 (d, J=8.6 Hz, 2H), 3.97 (t, J=6.3 Hz, 2H), 3.61 (d, J=13.4 Hz, 1H), 3.13 (m, 1H), 2.97 (m, 1H), 2.79 (d, J=13.4 Hz, 1H), 2.48 (m, 2H), 2.41 (br, 4H), 2.01-1.98 (m, 5H), 2.01-1.89 (m, 3H), 1.82-1.72 (m, 2H) 1.63-1.51 (m, 4H), 1.48-1.39 (m, 2H).

Workup

  1. extractionextracted with DCM (3×10 mL)
  2. dry with materialThe combined organic phases were dried (sodium sulfate)
  3. customevaporated

Sources & evidence

ORD record
ord-526af58d26574d8fb6dc096b74f10d09
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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