Benzylamine → HCID 46936143, compound

HRID 1754826Notes

Reaction equation

HRID 1754826 reaction equation
Cl[CH:2]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][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][CH3:60])=[CH:34][CH:33]=1)[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:5][CH:4]=1.[CH2:61]([NH2:68])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1.C(N(C(C)C)C(C)C)C>C(Cl)(Cl)Cl>[CH2:61]([NH:68][CH:2]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][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][CH3:60])=[CH:34][CH:33]=1)[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:5][CH:4]=1)[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 66717823HCID 66717823, compound

Product 1

HCID 46936143HCID 46936143, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To chloro-bis(4-docosyloxyphenyl)methane (75.9 mg, 89.1 μmol) were added chloroform (1 ml), benzylamine (29.1 μl, 267 μmol) and N-ethyldiisopropylamine (45.7 μl, 267 μmol), and the mixture was stirred at room temperature overnight. The reaction mixture was warmed to 50° C. and stirred for 1 hr. The mixture was cooled to room temperature again, and washed successively with 0.5N hydrochloric acid, 10% aqueous sodium hydrogen carbonate and 20% brine. The organic layer was dehydrated with anhydrous sodium sulfate, chloroform was evaporated, and the residue was precipitated with methanol to give N-benzyl-[bis(4-docosyloxyphenyl)]methylamine (72 mg, 87%).

Workup

  1. temperatureThe reaction mixture was warmed to 50° C.
  2. stirringstirred for 1 hr
  3. temperatureThe mixture was cooled to room temperature again
  4. washwashed successively with 0.5N hydrochloric acid, 10% aqueous sodium hydrogen carbonate and 20% brine
  5. customwas evaporated
  6. customthe residue was precipitated with methanol

Sources & evidence

ORD record
ord-95625b06ae52437e83501934212f06bb
Source dataset
uspto-grants-2015_10
Patent number
US09169187B2

Reaction notes

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