Dabco → HCID 21539312, compound

HRID 1076220Notes

Reaction equation

HRID 1076220 reaction equation
[CH2:1]1[C:6]2([C:15](=[O:16])[NH:14][C:8]3([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:17]1([N:23]=[C:24]=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.N12CCN(CC1)CC2>C1C=CC=CC=1>[CH:17]1([NH:23][C:24]([N:14]2[C:15](=[O:16])[C:6]3([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5]3)[NH:7][C:8]32[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 9237DabcoHCID 18502Cyclohexyl isocyanateHCID 965547,14-Diazadispiro(5.1.5.2)pentadecan-15-one

Product 1

HCID 21539312HCID 21539312, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

11.1 Parts of 7,14-diazadispiro[5.1.5.2]pentadecan-15-one, 6.88 parts of cyclohexyl isocyanate and a trace of 1,4-diazabicyclo[2.2.2]octane in 150 parts of dry benzene were heated at reflux for 30 hours, cooled and filtered to remove N,N'-dicyclohexyl urea. The benzene filtrate was evaporated to dryness and the residue crystallised from petroleum ether of boiling range 80°-100°C to give 2.60 parts of 14-cyclohexylcarbamoyl-7,14-diazadispiro[5.1.5.2]pentadecan-15-one having a melting point of 106° to 109°C and the following analysis by weight:

Workup

  1. temperatureat reflux for 30 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customto remove N,N'-dicyclohexyl urea
  5. customThe benzene filtrate was evaporated to dryness
  6. customthe residue crystallised from petroleum ether of boiling range 80°-100°C

Sources & evidence

ORD record
ord-bc8594136485475db09a40b4df9f03a8
Source dataset
uspto-grants-1976_05
Patent number
US03956310

Reaction notes

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