Pyridine → 4-[6-(4-Nitro-phenoxycarbonyloxy)-hexylcarbamoyloxy]-piperidine-1-carboxylic acid 4-phenoxyphenyl ester

HRID 618288Notes

Reaction equation

HRID 618288 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33])=[O:25])[CH2:19][CH2:18]2)=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:41]([O:43][C:44]1[CH:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][CH:45]=1)=[O:42]>C(Cl)Cl>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([O:23][C:24](=[O:25])[NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:41]([O:43][C:44]3[CH:45]=[CH:46][C:47]([N+:50]([O-:52])=[O:51])=[CH:48][CH:49]=3)=[O:42])[CH2:19][CH2:18]2)=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 537895824-[[[(6-Hydroxyhexyl)amino]-carbonyl]oxy]-1-piperidinecarboxylic acid 4-phenoxyphenyl ester

Product 1

HCID 542367634-[6-(4-Nitro-phenoxycarbonyloxy)-hexylcarbamoyloxy]-piperidine-1-carboxylic acid 4-phenoxyphenyl esterYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the alcohol (40.0 g, 88 mmol) produced in Example 4 and pyridine (7.1 ml, 88 mmol) in 300 ml of methylene chloride was added under nitrogen dropwise over one hour to a solution of 4-nitrophenyl chloroformate (17.7 g, 88 mmol) in 300 ml of methylene chloride at ice bath temperature. The reaction was stirred at ice bath temperature for two hours and 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 54.9 g of an off-white solid. Recrystallization from 1:1 ethyl acetatehexane gave 51.6 g (95%) of the title compound as a white crystalline solid, mp 117-120° C.

Workup

  1. customovernight
  2. customat room temperature
  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-802a19b88eea45a6a9e78983f4d34ed8
Source dataset
uspto-grants-1999_09
Patent number
US05952354

Reaction notes

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