3,5-Dichlorophenyl isocyanate → HCID 68534877, compound

HRID 2180188Notes

Reaction equation

HRID 2180188 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=2)([CH2:14][NH:15][CH3:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]1[CH:26]=[C:27]([N:32]=[C:33]=[O:34])[CH:28]=[C:29]([Cl:31])[CH:30]=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:14][N:15]([CH3:16])[C:33]([NH:32][C:27]2[CH:26]=[C:25]([Cl:24])[CH:30]=[C:29]([Cl:31])[CH:28]=2)=[O:34])([C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 207794724-(4-Iodo-phenyl)-4-methylaminomethyl-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68534877HCID 68534877, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(4-Iodo-phenyl)-4-methylaminomethyl-piperidine-1-carboxylic acid tert-butyl ester (0.15 g, 0.35 mmol) was dissolved in CH2Cl2 (2 mL) and 3,5-dichlorophenylisocyanate (0.066 g, 0.35 mmol, 1 eq.) was added. The reaction was stirred at room temperature for 6 h, diluted with CH2Cl2 (25 mL) and washed with saturated brine (25 mL). The aqueous layer was washed with CH2Cl2 (2×20 mL). The combined organic extracts were washed with saturated brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated by rotary evaporation to give 4-[3-(3,5-dichloro-phenyl)-1-methyl-ureidomethyl]-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.218 g, 100%). 1H NMR (CDCl3): δ 7.84 (d, 2H), 7.24 (m, 3H), 7.09 (m, 2H), 6.23 (br.s, 1H), 3.96 (d, 2H), 3.54 (s, 2H), 2.99 (dd, 2H), 2.70 (s, 3H), 2.28 (d, 2H), 1.90m (dd, 3H), 1.54 (s, 9H).

Workup

  1. washwashed with saturated brine (25 mL)
  2. washThe aqueous layer was washed with CH2Cl2 (2×20 mL)
  3. washThe combined organic extracts were washed with saturated brine (20 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-6bf2e4ccdcbc4dab8f31b3ab8257529c
Source dataset
uspto-grants-2005_05
Patent number
US06887889B2

Reaction notes

Loading…