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

HRID 723588Notes

Reaction equation

HRID 723588 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 vacuo. The crude product was chromatographed on silica gel, eluting with 2% methanovdichloromethane 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% methanovdichloromethane
  8. additioncontaining 0.01% ammonium hydroxide

Sources & evidence

ORD record
ord-f6d9298b57e44ed78c4b44bac8221de5
Source dataset
uspto-grants-2006_11
Patent number
US07141584B2

Reaction notes

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