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

HRID 634833Notes

Reaction equation

HRID 634833 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]>>[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

3

Reactant 2

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

Product 1

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

Procedure

A solution of 4-(piperidin-4-ylmethyl)-phenylamine (0.57 g, 3 mmol) in dicholoromethane (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 vacua. 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 vacua
  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-e239ed6d5fbb4eebb0a96d4d0c1ec0f0
Source dataset
uspto-grants-2001_02
Patent number
US06184242B2

Reaction notes

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