Isopropyl isocyanate → 4-(1-Isopropylaminocarbonylpiperidin-4-ylmethyl)-phenylamine

HRID 993408Notes

Reaction equation

HRID 993408 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[CH:15]([N:18]=[C:19]=[O:20])([CH3:17])[CH3:16]>ClCCl>[CH:15]([NH:18][C:19]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=2)[CH2:3][CH2:2]1)=[O:20])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 109978244-[(Piperidin-4-yl)methyl]aniline

Product 1

HCID 218768574-(1-Isopropylaminocarbonylpiperidin-4-ylmethyl)-phenylamineYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(piperidin-4-ylmethyl)-phenylamine (0.57 g, 3 mmol) in dichloromethane (20 mL) was cooled in an ice bath under nitrogen atmosphere. Isopropyl isocyanate (0.28 g, 3.3 mmol) was added dropwise to the solution and stirred at ice bath temperature for 30 minutes. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic extracts were washed with water and brine, dried, and solvents removed in vacuo. The crude product was chromatographed on silica gel, eluting with 2% methanol/dichloromethane containing 0.01% ammonium hydroxide, to give 4-(1-isopropylaminocarbonylpiperidin-4-ylmethyl)-phenylamine (0.66 g, 80%) as a gum.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with dichloromethane
  3. washThe combined organic extracts were washed with water and brine
  4. customdried
  5. customsolvents removed in vacuo
  6. customThe crude product was chromatographed on silica gel
  7. washeluting with 2% methanol/dichloromethane containing 0.01% ammonium hydroxide

Sources & evidence

ORD record
ord-65d37e6e0ef14b2895da35145511fc7e
Source dataset
uspto-grants-2002_10
Patent number
US06472536B1

Reaction notes

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