Dimethylformamide → HCID 11625795, compound

HRID 2371141Notes

Reaction equation

HRID 2371141 reaction equation
Cl.Cl.[CH2:3]([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][C:12]2([OH:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:6]1)[CH3:4].C(N(C(C)C)CC)(C)C.CN(C)C=O.[Cl:33][C:34]1[CH:35]=[C:36]([N:41]=[C:42]=[O:43])[CH:37]=[CH:38][C:39]=1[Cl:40]>ClCCl>[Cl:33][C:34]1[CH:35]=[C:36]([NH:41][C:42]([N:15]2[CH2:14][CH2:13][C:12]([CH2:11][CH:7]3[CH2:8][CH2:9][CH2:10][N:5]([CH2:3][CH3:4])[CH2:6]3)([OH:18])[CH2:17][CH2:16]2)=[O:43])[CH:37]=[CH:38][C:39]=1[Cl:40]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 76073,4-Dichlorophenyl isocyanateHCID 81531DiisopropylethylamineHCID 67221027HCID 67221027, compound

Product 1

HCID 11625795HCID 11625795, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[(1-ethylpiperidin-3-yl)methyl]piperidin-4-ol dihydrochloride (80 mg) in dichloromethane (10 mL) was added di-iso-propylethylamine (0.12 mL), dimethylformamide (1 mL) and 3,4-dichlorophenylisocyanate (55 mg). After 10 minutes the mixture was evaporated and the residue was purified by silica column chromatography, eluting with a gradient of 0 to 10% 7M NH3/MeOH in dichloromethane to give the title compound as a white solid (110 mg, 100%).

Workup

  1. customAfter 10 minutes the mixture was evaporated
  2. customthe residue was purified by silica column chromatography
  3. washeluting with a gradient of 0 to 10% 7M NH3/MeOH in dichloromethane

Sources & evidence

ORD record
ord-beb8f0762f0b4b1385813c0856e6da3c
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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