Piperidine → 4-(Piperidine-1-carbonyloxy)-piperidine-1-carboxylic acid 6-[(4-phenoxy-phenyl)oxycarbonylamino]-hexyl ester

HRID 260340Notes

Reaction equation

HRID 260340 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[O:14]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][C:38]([N:40]2[CH2:45][CH2:44][CH:43]([O:46][C:47]([O:49]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:42][CH2:41]2)=[O:39])=[O:29])=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[O:14]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][C:38]([N:40]2[CH2:41][CH2:42][CH:43]([O:46][C:47]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:49])[CH2:44][CH2:45]2)=[O:39])=[O:29])=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 152933074-(4-Nitro-phenoxycarbonyloxy)-piperidine-1-carboxylic acid 6-[(4-phenoxy-phenyl)-oxycarbonylamino]-hexyl ester

Product 1

HCID 541283684-(Piperidine-1-carbonyloxy)-piperidine-1-carboxylic acid 6-[(4-phenoxy-phenyl)oxycarbonylamino]-hexyl esterYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of piperidine (382 μl, 3.86 mmol) and triethylamine (2.24 mL, 16.1 mmol) in 30 mL of methylene chloride was added under nitrogen dropwise to a solution of the carbonate prepared in Example 5 (2.0 g, 3.22 mmol) in 30 mL of methylene chloride at ice bath temperature. After the addition the cooling bath was removed and the reaction stirred at room temperature overnight. 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 1.85 g of an oil. Purification of the oil on silica gel (230-400 mesh) using 5%-20% ethyl acetate-methylene chloride as the eluent gave 1.23 g (68%) of the title compound as a white crystalline solid, mp 56°-61° C.

Workup

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

Sources & evidence

ORD record
ord-7cd6f0f027fd4a479ba799f121b2b9a1
Source dataset
uspto-grants-1996_06
Patent number
US05527804

Reaction notes

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