Triethylamine → (4-Phenoxyphenyl) 4-hydroxypiperidine-1-carboxylate

HRID 618285Notes

Reaction equation

HRID 618285 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:26])OC2C=CC([N+]([O-])=O)=CC=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(N(CC)CC)C>C(Cl)Cl>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]([N:31]2[CH2:32][CH2:33][CH:28]([OH:27])[CH2:29][CH2:30]2)=[O:26])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 54343370Carbonic Acid (4-nitrophenyl)ester (4-phenoxy-phenyl)ester

Product 1

HCID 2729092(4-Phenoxyphenyl) 4-hydroxypiperidine-1-carboxylateYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the carbonate(45 g, 0.13 mol) produced in Example 1 in 250 mL of methylene chloride was added dropwise under nitrogen over three hours to a solution of 4-hydroxypiperidine (14.3 g, 0.14 mol) and triethylamine (19.7 mL, 0.14 mol) in 250 mL of methylene chloride at ice bath temperature. After the addition the reaction was stirred at ice bath temperature for 4 hours and at room temperature overnight. The reaction was extracted one time with 1N HCl and then multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 39.27 g of a light yellow solid. Recrystallization from diisopropyl ether-methanol gave 31.78 g (79%) of the title compound as an off-white crystalline solid, mp 130-133° C.

Workup

  1. additionAfter the addition the reaction
  2. customat room temperature
  3. customovernight
  4. extractionThe reaction was extracted one time with 1N HCl
  5. dry with materialmultiple times with saturated Na2CO3, dried (MgSO4)
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-8e587cc2585a4de493af18477aba9cea
Source dataset
uspto-grants-1999_09
Patent number
US05952354

Reaction notes

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