Piperidine → 2,3,4-Tris(octadecyloxy)benzhydryl amine

HRID 573967Notes

Reaction equation

HRID 573967 reaction equation
C1C2C(COC([NH:18][CH:19]([C:83]3[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=3)[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[C:22]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[C:21]=3[O:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH3:82])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C(Cl)(Cl)Cl.C(#N)C>[CH2:65]([O:64][C:21]1[C:22]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])=[C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:24]=[CH:25][C:20]=1[CH:19]([NH2:18])[C:83]1[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=1)[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH3:82]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 59510359N-Fmoc-[phenyl(2,3,4-trioctadecanoxyphenyl)methyl]amine

Product 1

HCID 469361412,3,4-Tris(octadecyloxy)benzhydryl amineYield 98%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

N-(9-Fluorenylmethoxycarbonyl)-2,3,4-tris(octadecyloxy)benzhydryl amine (3.37 g, 2.89 mmol) was dissolved in a mixed solvent of chloroform (30 mL) and acetonitrile (15 mL), 20% piperidine [1-methyl-2-pyrrolidone solution] (28.6 mL, 57.9 mmol) was added, and the mixture was stirred at room temperature for 30 min. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, methanol was added, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure to give the title compound (2.80 g, 97.9%) as a white solid.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure, methanol
  4. additionwas added
  5. filtrationthe precipitated solid was collected by filtration
  6. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-f3fa4eab4f7f424d9c4f1615444d0221
Source dataset
uspto-grants-2015_05
Patent number
US09029528B2

Reaction notes

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