Piperidine → HCID 131728472, compound

HRID 1927489Notes

Reaction equation

HRID 1927489 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH3:33])[C:14]2[O:20][C:19]3[C:21]([Cl:29])=[CH:22][C:23]([NH:25][CH2:26][CH2:27]Cl)=[CH:24][C:18]=3[CH2:17][S:16](=[O:31])(=[O:30])[C:15]=2[CH:32]=1)=[O:10]>CN(C=O)C>[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH3:33])[C:14]2[O:20][C:19]3[C:21]([Cl:29])=[CH:22][C:23]([NH:25][CH2:26][CH2:27][N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:24][C:18]=3[CH2:17][S:16](=[O:30])(=[O:31])[C:15]=2[CH:32]=1)=[O:10]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 1317284464-Chloro-2-(2-chloro-ethylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]-cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 131728472HCID 131728472, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Piperidine (0.184 g, 2.16 mmol) was added with stirring to a solution of Example 56k (0.6 g, 1.4 mmol) in DMF (1 mL) in an inert atmosphere and heated at 90° C. for 4 h. The reaction mixture was concentrated, treated with water, and the solid that precipitated was filtered, washed with water and purified using flash chromatography (silica gel, 2% methanol/chloroform) to obtain the title compound. Yield: 0.330 g, (48%); 1H NMR (CDCl3,): δ 1.18 (bs, 2H, CH2), 1.32 (t, 4H, 2CH2), 2.21 (s, 3H, CH3), 2.3 (t, 2H, CH2), 2.4 (t, 2H, CH2), 2.8 (m, 4H, 2CH2), 3.41 (s, 3H, OCH3), 4.28 (s, 2H, CH2), 5.39 (bs, 1H, NH), 6.15 (s, 2H, Ar), 7.6 (s, 1H, Ar). 7.82 (s, 1H, Ar); MS: m/e (ES+) 478 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiontreated with water
  3. customthe solid that precipitated
  4. filtrationwas filtered
  5. washwashed with water
  6. custompurified

Sources & evidence

ORD record
ord-6c139d73859442839546e0e8838ac558
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

Loading…