1,4'-Bipiperidine → HCID 86753925, compound

HRID 1418698Notes

Reaction equation

HRID 1418698 reaction equation
[I:1][CH2:2][C:3]([O:5][CH:6]([C:9]1[CH:25]=[C:24]2[N:12]([CH2:13][C:14]3[C:15]2=[N:16][C:17]2[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11](=[O:26])[C:10]=1[CH3:27])[CH2:7][CH3:8])=[O:4].[N:28]1([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>C(Cl)Cl>[IH:1].[N:28]1([CH:34]2[CH2:39][CH2:38][N:37]([CH2:2][C:3]([O:5][CH:6]([C:9]3[CH:25]=[C:24]4[N:12]([CH2:13][C:14]5[C:15]4=[N:16][C:17]4[C:22]([CH:23]=5)=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:11](=[O:26])[C:10]=3[CH3:27])[CH2:7][CH3:8])=[O:4])[CH2:36][CH2:35]2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 786071,4'-Bipiperidine2×HCID 86753922HCID 86753922, compound

Product 1

HCID 86753925HCID 86753925, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (±)-7-[1-[(iodoacetyl)oxy]propyl]-8-methylindolizino[1,2-b]quinolin-9(11H)-one (50 mg, 0.11 mmol) in CH2Cl2 (4 mL) was added 4-piperidinopiperidine (17.6 mg, 0.11 mmol). After stirring at room temperature for 3.5 h, thin layer chromatographic analysis indicated that the reaction was incomplete,. Additional 4-piperidinopiperidine (2.7 mg, 0.016 mmol) was added, and stirring was continued for 2 d. The mixture was concentrated under reduced pressure, and the residue was purified by column chromatography eluting with a solvent gradient of 0-100% MeOH in H2O containing 1% HOAc. The title compound was obtained after lyophilization. 1H NMR (CDCl3) d 8.35 (s, 1H), 8.21 (d, J=8.4 Hz, 1H), 7.92 (d, J=8.3 Hz, 1H), 7.83 (m, 1H), 7.63 (m, 1H), 7.34 (s, 1H), 5.94 (apparent t, 1H), 5.26 (s, 2H), 3.32 (s, 2H), 3.00 (br m, 2H), 2.37 (s, 3H), 2.6-1.4 (m, 13H), 0.98 (t, J=7.4 Hz, 3H). Anal. Calcd for C31H38N4O3.1/4 HI.3/8 H2O: C, 67.28; H, 7.10; N, 10.12. Found: C, 67.67; H, 6.79; N, 9.69.

Workup

  1. stirringstirring
  2. waitwas continued for 2 d
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography
  5. washeluting with a solvent gradient of 0-100% MeOH in H2O containing 1% HOAc

Sources & evidence

ORD record
ord-2510321bc5dc4b5aa2062697acdc1eec
Source dataset
uspto-grants-1999_03
Patent number
US05883255

Reaction notes

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