Potassium Carbonate → HCID 22260066, compound

HRID 1609817Notes

Reaction equation

HRID 1609817 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][CH:13]3[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.Cl[CH2:20][C:21]1[CH:29]=[CH:28][C:24]2[O:25][CH2:26][O:27][C:23]=2[CH:22]=1.C([O-])([O-])=O.[K+].[K+].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>CN(C=O)C.C(Cl)Cl.CO>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([NH:12][CH:13]3[CH2:18][CH2:17][CH2:16][N:15]([CH2:20][C:21]4[CH:29]=[CH:28][C:24]5[O:25][CH2:26][O:27][C:23]=5[CH:22]=4)[CH2:14]3)=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 1859152-NaphthylalanineHCID 22260058HCID 22260058, compound

Product 1

HCID 22260066HCID 22260066, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

3-[(4-(Imidazol-1-yl)phenyl)amino]piperidine (330 mg, 1.36 mmol) was dissolved in DMF and then treated with 5-chloromethyl-1,3-benzodioxole (1.0 eq.), K2CO3 (2.5 eq.) and Nal (0.1 eq.). The resulting mixture was heated at 50° C. for 1 hour. Filtration of the mixture and evaporation of the solvent in vacuo gave a crude product (411 mg). Flash column chromatography on silical gel with 1-2.5% methanol in methylene chloride afforded 3-[(4-(imidazol-1-yl)phenyl)amino]-1-[(1,3-benzodioxol-5-yl)methyl]piperidine (110 mg), 1H NMR(CDCl3) 7.70 (s, 1), 7.10 (m, 4), 6.80 (s, 1), 6.70 (m, 2), 6.60 (d, 2), 5.90 (s, 2), 4.30 (m, 1), 3.60 (m, 1), 3.40 (AB q, 2), 2.70 (m, 1), 2.40 (m, 3), 1.50-1.80 (m, 4) ppm.

Workup

  1. filtrationFiltration of the mixture and evaporation of the solvent in vacuo
  2. customgave a crude product (411 mg)

Sources & evidence

ORD record
ord-113a06404d064033bef42e9f5121d195
Source dataset
uspto-grants-2006_01
Patent number
US06982259B2

Reaction notes

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