Potassium Carbonate → HCID 59837491, compound

HRID 272905Notes

Reaction equation

HRID 272905 reaction equation
N1(CCC[O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)CCCC1.Cl[CH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([OH:34])[CH2:30][CH2:29]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:34][CH:31]1[CH2:32][CH2:33][N:28]([CH2:27][CH2:26][CH2:25][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127257181-(3-Chloropropyl)piperidin-4-olHCID 598373944-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile

Product 1

HCID 59837491HCID 59837491, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile (533 mg, 2.62 mmol), 1-(3-chloro-propyl)-piperidin-4-ol (750 mg, 4.22 mmol), DMF (10 ml) and K2CO3 (1.44 g, 10.42 mmol) were reacted together according to general procedure E. Purification by chromatography on silica, eluant DCM:MeOH:NH3 (92:6:2) provided the title compound (550 mg, 61%) as an off white solid. 1H NMR (400 MHz, CDCl3), δ 7.38 (d, 2H), 6.93 (d, 2H), 4.13-4.04 (m, 2H), 4.02 (t, 2H), 3.89 (td, 2H), 3.70 (m, 1H), 2.87-2.71 (m, 2H), 2.50 (t, 2H), 2.23-1.84 (m, 10H), 1.68-1.49 (m, 3H).

Workup

  1. customPurification by chromatography on silica, eluant DCM:MeOH:NH3 (92:6:2)

Sources & evidence

ORD record
ord-416e07b8099b40229b3e62a8aba82260
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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