(3S)-Piperidin-3-amine--hydrogen chloride (1/2) → HCID 59768630, compound

HRID 2217847Notes

Reaction equation

HRID 2217847 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:8]([C:12]([NH:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:13])=[C:7]([Cl:22])[CH:6]=[CH:5][C:4]=2[N:3]=1.Cl.Cl.[NH:25]1[CH2:30][CH2:29][CH2:28][C@H:27]([NH2:31])[CH2:26]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[NH2:31][C@H:27]1[CH2:28][CH2:29][CH2:30][N:25]([C:2]2[CH:11]=[CH:10][C:9]3[C:8]([C:12]([NH:14][CH2:15][CH:16]4[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)=[O:13])=[C:7]([Cl:22])[CH:6]=[CH:5][C:4]=3[N:3]=2)[CH2:26]1

Participants

5

Reactant 2

HCID 16218278(3S)-Piperidin-3-amine--hydrogen chloride (1/2)HCID 860130222,6-dichloro-N-(cyclohexylmethyl)-5-quinolinecarboxamide

Product 1

HCID 59768630HCID 59768630, compoundYield 40.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

A stirred suspension of 2,6-dichloro-N-(cyclohexylmethyl)quinoline-5-carboxamide (Example 43(a)) (250 mg), (3S)-3-piperidinamine dihydrochloride (260 mg) and tetrabutylammonium bromide (20 mg) in acetonitrile (2 mL) was heated at 130° C. in a microwave for 90 minutes after which it was cooled to room temperature and concentrated. The residue was purified by chromatography (SiO2, dichloromethane:methanol:ammonia in methanol (7 M) 96:3:1 as eluant) and subsequent recrystallisation (acetonitrile) gave the title compound as a solid (120 mg).

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography (SiO2, dichloromethane:methanol:ammonia in methanol (7 M) 96:3:1 as eluant) and subsequent recrystallisation (acetonitrile)

Sources & evidence

ORD record
ord-98d1725d0f1f423fa1488e031f35f95e
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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