Water → HCID 131710579, compound

HRID 1973816Notes

Reaction equation

HRID 1973816 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:10]=[C:11]([N:14]([C:21]1([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][CH3:13].C(N(CC)CC)C.CN(C)C(=[O:43])C.[OH2:45]>>[OH2:10].[C:27]([OH:29])(=[O:28])[C:21]([OH:43])=[O:45].[O:10]=[C:11]([N:14]([C:21]1([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:26][CH2:25][N:24]([CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][CH3:13].[CH2:30]([O:29][C:27]([C:21]1([N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11](=[O:10])[CH2:12][CH3:13])[CH2:26][CH2:25][N:24]([CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:23][CH2:22]1)=[O:28])[CH3:31].[C:27]([OH:29])(=[O:28])[C:21]([OH:43])=[O:45]

Participants

6

Reactant 5

HCID 962WaterHCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 31374DimethylacetamideHCID 12298181HCID 12298181, compound

Product 1

HCID 131710579HCID 131710579, compound

Conditions

Temperature
70 °C

Procedure

A mixture of 3.1 parts of (2-bromoethyl)benzene, 4.6 parts of ethyl 4-[N-(1-oxopropyl)-N-phenylamino]-4-piperidinecarboxylate, 2.7 parts of N,N-diethylethanamine and 67.5 parts of N,N-dimethylacetamide is stirred for 2 hours at 70° C. The reaction mixture is poured onto 600 parts of water, whereupon an oil is precipitated. The supernatant phase is decanted and discarded. The oily product is dissolved in 210 parts of 1,1'-oxybispropane. The solution is washed twice with water, dried, filtered and evaporated. The residue is converted into the ethanedioate salt in 2-propanol. The salt is filtered off and dried at 120° C, yielding ethyl 4-[N-(1-oxopropyl)-N-phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxylate ethanedioate hemihydrate; mp. 197.1° C.

Workup

  1. customis precipitated
  2. customThe supernatant phase is decanted
  3. dissolutionThe oily product is dissolved in 210 parts of 1,1'-oxybispropane
  4. washThe solution is washed twice with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe salt is filtered off
  9. customdried at 120° C

Sources & evidence

ORD record
ord-63455280e58b45ad9a18efd9640ba8bb
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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