Cyclohexyl isocyanate → HCID 178525918, compound

HRID 2410060Notes

Reaction equation

HRID 2410060 reaction equation
[CH:1]1([N:7]2[C:12](=[O:13])[CH2:11][C:10](=[O:14])[N:9]([CH:15]3[CH2:20][CH2:19][CH2:18][N:17](C(OCC4C=CC=CC=4)=O)[CH2:16]3)[C:8]2=[O:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.NC1CCC[N:36]([C:40](OCC2C=CC=CC=2)=[O:41])C1.C(N(C(C)C)CC)(C)C.C1(N=C=[O:67])CCCCC1.C(Cl)(=O)[CH2:69][C:70](Cl)=[O:71]>ClCCl>[CH:1]1([N:7]2[C:12](=[O:13])[C:11]([C:40]([NH:36][CH2:69][C:70]([OH:71])=[O:67])=[O:41])=[C:10]([OH:14])[N:9]([CH:15]3[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]3)[C:8]2=[O:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 18502Cyclohexyl isocyanateHCID 74269Propanedioyl dichlorideHCID 81531DiisopropylethylamineHCID 17750333Benzyl 3-aminopiperidine-1-carboxylate--hydrogen chloride (1/1)HCID 68636396Phenylmethyl 3-(3-cyclohexyl-2,4,6-trioxotetrahydro-1(2H)-pyrimidinyl)-1-piperidinecarboxylate

Product 1

HCID 178525918HCID 178525918, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylmethyl 3-(3-cyclohexyl-2,4,6-trioxotetrahydro-1(2H)-pyrimidinyl)-1-piperidinecarboxylate. A mixture of benzyl 3-aminopiperidine-1-carboxylate hydrochloride (1.51 g, 5.57 mmoles), diisopropylethylamine (965 uL, 5.57 mmoles) and cyclohexylisocyanate (708 uL, 5.57 mmoles) were stirred together in dichloromethane (60 mL) overnight. The mixture was washed with 1 molar hydrochloric acid (×2) and the solution dried. Malonyl dichloride (650 uL, 6.68 mmoles) was added and the mixture was heated under gentle reflux for 4 hours. The mixture was washed with 1 molar hydrochloric acid (×2) and the solution dried and evaporated. The title compound was obtained as a solid from diethyl ether (1.0 g, 42%). 1H NMR (400 MHz, DMSO-d6) ppm 7.24-7.47 (m, 5 H), 5.09 (s, 2 H), 4.35-4.58 (m, 2 H), 3.98 (d, 2 H), 3.68 (d, J=4.29 Hz, 2 H), 3.35-3.60 (m, 1 H), 2.32 (q, 1 H), 2.07-2.21 (m, 2 H), 1.66-1.87 (m, 5 H), 1.53-1.65 (m, 3 H), 1.36-1.50 (m, 1 H), 1.26 (q, J=13.05 Hz, 2 H), 1.03-1.15 (m, 1 H)

Workup

  1. washThe mixture was washed with 1 molar hydrochloric acid (×2)
  2. customthe solution dried
  3. temperaturethe mixture was heated
  4. temperatureunder gentle reflux for 4 hours
  5. washThe mixture was washed with 1 molar hydrochloric acid (×2)
  6. customthe solution dried
  7. customevaporated

Sources & evidence

ORD record
ord-2e087d9d1235498f8ea783eda5f5c366
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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