1-Aminopiperidine → HCID 21955075, compound

HRID 25188

Reaction equation

HRID 25188 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=2)[N:9]2[CH2:12][C:11](=[C:13]([S:34]([CH3:37])(=[O:36])=[O:35])[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20](OC4C(F)=C(F)C(F)=C(F)C=4F)=[O:21])[CH:15]=3)[CH2:10]2)=[CH:4][CH:3]=1.[NH2:45][N:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1>CN(C)C=O.C(OCC)(=O)C>[Cl:44][C:41]1[CH:42]=[CH:43][C:38]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:9]2[CH2:12][C:11](=[C:13]([S:34]([CH3:37])(=[O:35])=[O:36])[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=[O:21])[NH:45][N:46]4[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]4)[CH:15]=3)[CH2:10]2)=[CH:39][CH:40]=1

Participants

5

Reactant 2

HCID 166581-AminopiperidineHCID 225653571-[Bis(4-chlorophenyl)methyl]-3-{(methylsulfonyl)[3-(pentafluorophenoxycarbonyl)phenyl]methylene]azetidine

Product 1

HCID 21955075HCID 21955075, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.45 g of 1-[bis(4-chlorophenyl)methyl]-3-{(methylsulfonyl)[3-(pentafluorophenoxycarbonyl)phenyl]methylene}azetidine, 0.07 cm3 of 1-aminopiperidine in 4 cm3 of dimethylformamide is stirred for 18 hours at room temperature. The mixture is taken up in 30 cm3 of ethyl acetate. The organic phase is washed with 3 times 50 cm3 of water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). 0.2 g of 1-[bis-(4-chlorophenyl)methyl]-3-{(methylsulfonyl)[3-(N-piperidylcarbamoyl)phenyl]methylene}azetidine is obtained melting at 175° C. [NMR spectrum in DMSO-d6, T=300K, δ in ppm (400 MHz): 1.40 (2H, m, CH2), 1.60 (4H, m, 2CH2), 2.85 (4H, m, 2NCH2), 3.00 (3H, s, SCH3), 3.80 (2H, s, NCH2), 4.20 (2H, s, NCH2), 4.80 (1H, s, NCH), between 7.45 and 7.60 (10H, m, 10CH arom.), 7.75 (2H, m, 2CH arom.), 9.45 (1H, s, NH)].

Workup

  1. washThe organic phase is washed with 3 times 50 cm3 of water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-8cecdbfffc7b45f996c5cc2e6af9614a
Source dataset
uspto-grants-2005_02
Patent number
US06858603B2

Linked notes

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