HCID 11673521, compound → HCID 19071332, compound

HRID 1955632Notes

Reaction equation

HRID 1955632 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10]([NH:12][CH2:13][CH2:14][C:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>CO.O.[Pd]>[CH:15]1([CH2:14][CH2:13][NH:12][C:10]([NH:9][CH2:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:11])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 1

HCID 11673521HCID 11673521, compound

Product 1

HCID 19071332HCID 19071332, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1,3-Bis[2-(1-cyclohexen-1-yl)ethyl]urea (from step (a) example 8, 10.82 g, 39.14 mmol) was dissolved in methanol (400 mL)-water (12 mL) and shaken with 10% palladium on carbon (600 mg) under hydrogen (55 psi) on a Parr apparatus for 7.5 h. The catalyst was filtered off (Celite) and volatiles were removed in vacuo to leave 1,3-bis(2-cyclohexylethyl)urea as white crystals (10.72 g, 98%), m.p. 150°-151.5° C.; 1H-NMR (DMSO-d6) consistent with structure.

Workup

  1. filtrationThe catalyst was filtered off (Celite) and volatiles
  2. customwere removed in vacuo

Sources & evidence

ORD record
ord-9bded480f87d491e93bddd6785aea065
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

Loading…