Ammonia → HCID 20083492, compound

HRID 1609212Notes

Reaction equation

HRID 1609212 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]#[N:32])=[CH:21][CH:20]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:42](Cl)(=[O:47])[CH2:43][CH2:44][CH2:45][CH3:46].N>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([C:11]1([N:17]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]#[N:32])=[CH:23][CH:24]=2)[C:42](=[O:47])[CH2:43][CH2:44][CH2:45][CH3:46])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 61186Valeryl chlorideHCID 81531DiisopropylethylamineHCID 20083502HCID 20083502, compound

Product 1

HCID 20083492HCID 20083492, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.9 g (6.8 mmol) of N-(1-benzyloxycarbonylcyclohexyl)-N-(2'-cyanobiphenyl-4-ylmethyl)-amine and 4.4 ml (26 mmol) of Hunig base in 50 ml of ethyl acetate is treated with 1.1 g (9 mmol) of pentanoyl chloride, and the mixture is heated to reflux for 24 hours. After cooling, the reaction mixture is treated with 20 ml of aqueous ammonia solution (2N) and stirred for 1 hour. The organic phase is separated, washed in succession with 2 N-hydrochloric acid, saturated sodium hydrogencarbonate solution and brine, dried and evaporated. The N-(1-benzyloxycarbonylcyclohexyl)-N-(2'-cyanobiphenyl-4-ylmethyl)-N-pentanoyl-amine is thus obtained in the form of a brown oil [Rf : 0.44 (toluene/methanol=19:1)], which is used for further reactions in crude form.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 24 hours
  3. temperatureAfter cooling
  4. customThe organic phase is separated
  5. washwashed in succession with 2 N-hydrochloric acid, saturated sodium hydrogencarbonate solution and brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-cd0a845d66b2487387bee7f23f2719e6
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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