Diisopropylethylamine → HCID 18760289, compound

HRID 432824Notes

Reaction equation

HRID 432824 reaction equation
C(N1CCCC(C(OCC)=O)C1)(=O)C1C=CC=CC=1.[CH3:20][CH:21]1[CH2:26][NH:25][CH2:24][CH:23]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:22]1.C(N(C(C)C)CC)(C)C.[S:41]1[CH:45]=[CH:44][CH:43]=[C:42]1[CH2:46][C:47](Cl)=[O:48]>>[S:41]1[CH:45]=[CH:44][CH:43]=[C:42]1[CH2:46][C:47]([N:25]1[CH2:26][CH:21]([CH3:20])[CH2:22][CH:23]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:24]1)=[O:48]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 1623622-Thiopheneacetyl chlorideHCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylateHCID 13658604HCID 13658604, compound

Product 1

HCID 18760289HCID 18760289, compoundYield 74%

Procedure

This reaction was run in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with ethyl 5-methyl-3-piperidinecarboxylate (311 mg; 1.82 mmol), diisopropylethylamine (350 μl; 2.01 mmol), and thiopheneacetyl chloride (225 μl; 1.83 mmol). Crude product was purified by distillation at approximately 220° C./0.1 torr, giving ethyl 1-(2-thiopheneacetyl)-5-methyl-3-piperidinecarboxylate (398 mg) as a yellow oil. MS m/z (positive ion) 467 (25), 296 (MH+; 100).

Workup

  1. distillationCrude product was purified by distillation at approximately 220° C./0.1 torr

Sources & evidence

ORD record
ord-08542db8399844afb9210f8420216ea0
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Reaction notes

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