Diethylamine → n-[8-(4-Cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]oct-3-yl]-3-diethylaminopropionamide, hydrochloride

HRID 916355Notes

Reaction equation

HRID 916355 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([NH:6][CH:7]1[CH2:13][CH:12]2[N:14]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([C:25]#[N:26])=[CH:17][CH:16]=3)[CH:9]([CH2:10][CH2:11]2)[CH2:8]1)=[O:5].[CH2:27]([NH:29][CH2:30][CH3:31])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[ClH:1].[C:25]([C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([N:14]2[CH:12]3[CH2:11][CH2:10][CH:9]2[CH2:8][CH:7]([NH:6][C:4](=[O:5])[CH2:3][CH2:2][N:29]([CH2:30][CH3:31])[CH2:27][CH3:28])[CH2:13]3)=[CH:16][CH:17]=1)#[N:26]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 692265953-Chloro-N-[8-(4-cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]oct-3-yl]propanamide

Product 1

HCID 131726602n-[8-(4-Cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]oct-3-yl]-3-diethylaminopropionamide, hydrochlorideYield 19%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound (16 mg, 19%) was synthesized in the same way as 165RL52 using 165RL50 (80 mg, 0.21 mmol), diethylamine (45 μL, 0.44 mmol), potassium carbonate (60 mg, 0.44 mmol) and acetonitrile (6 mL).

Sources & evidence

ORD record
ord-5889cd25370d477883d3601c4fd0972b
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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