Triethylamine → HCID 15463329, compound

HRID 618289Notes

Reaction equation

HRID 618289 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](=[O:45])[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][C:33](OC3C=CC([N+]([O-])=O)=CC=3)=[O:34])[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.[CH3:46][C:47]([CH3:65])([CH3:64])[CH2:48][C:49]1[CH:63]=[CH:62][C:52]([CH2:53][NH:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])=[CH:51][CH:50]=1.C(N(CC)CC)C>CN(C)C=O.C(Cl)Cl>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]([N:17]2[CH2:18][CH2:19][CH:20]([O:23][C:24](=[O:45])[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][C:33](=[O:34])[N:54]([CH2:53][C:52]3[CH:62]=[CH:63][C:49]([CH2:48][C:47]([CH3:46])([CH3:65])[CH3:64])=[CH:50][CH:51]=3)[CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[CH2:21][CH2:22]2)=[O:16])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 14995484HCID 14995484, compoundHCID 542367634-[6-(4-Nitro-phenoxycarbonyloxy)-hexylcarbamoyloxy]-piperidine-1-carboxylic acid 4-phenoxyphenyl ester

Product 1

HCID 15463329HCID 15463329, compoundYield 112.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the carbonate (2.0 g, 3.2 mmol) produced in Example 5, 4-(2,2-dimethyl-propyl)-benzyl-heptylamine (1.1 g, 3.9 mmol) and triethylamine (2.2 ml, 16 mmol) in 30 ml of anhydrous dimethylformamide was stirred under nitrogen at room temperature overnight. The reaction was diluted with methylene chloride, extracted one time with 1N HCl, multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 2.73 g of a light brown oil. Purification of this oil by chromatography on silica gel (230-400 mesh) using 10% ethyl acetate-methylene chloride as the eluent gave 2.11 g (87%) of the title compound as a clear oil, MS m/e 758 (M+H)+.

Workup

  1. extractionextracted one time with 1N HCl, multiple times with saturated Na2CO3
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-140ef14d0f7f44d6b0862bf4e6fa461c
Source dataset
uspto-grants-1999_09
Patent number
US05952354

Reaction notes

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