Triethylamine → HCID 15293306, compound

HRID 260336Notes

Reaction equation

HRID 260336 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[O:15]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29](=[O:50])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][C:38](OC2C=CC([N+]([O-])=O)=CC=2)=[O:39])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[O:15]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][C:38]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[O:39])=[O:50])=[CH:24][CH:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 54063892HCID 54063892, compound

Product 1

HCID 15293306HCID 15293306, compoundYield 158.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-hydroxypiperidine (2.21 g, 21.8 mmol) and triethylamine (17.5 mL, 91 mmol) in 100 mL of methylene chloride was added under nitrogen dropwise to a solution of the carbonate prepared in Example 3 (9.0 g, 18.2 mmol) in 100 mL of methylene chloride at room temperature. After the addition the reaction was stirred overnight at room temperature. The reaction was extracted one time with 1N HCl, multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 13.16 g of a yellow oil. Purification of the oil on silica gel (230-400 mesh) using hexane-ethyl acetate as the eluent gave 5.87 g (71%) of the title compound as a white waxy solid, mp 48°-55° C.

Workup

  1. additionAfter the addition the reaction
  2. extractionThe reaction was extracted one time with 1N HCl, multiple times with saturated Na2CO3
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c43bc3e530364f0597b00eeeadf53554
Source dataset
uspto-grants-1996_06
Patent number
US05527804

Reaction notes

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