Triethylamine → HCID 19004150, compound

HRID 2226047Notes

Reaction equation

HRID 2226047 reaction equation
[C:1]([O:20][CH2:21][CH2:22][CH:23]1[CH2:28][N:27]([C:29]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:26][CH2:25][NH:24]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:55]1([N:61]([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[C:62](Cl)=[O:63])[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>CN(C)C=O>[C:55]1([N:61]([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[C:62]([N:24]2[CH2:25][CH2:26][N:27]([C:29]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:28][CH:23]2[CH2:22][CH2:21][O:20][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:63])[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65741N,N-Diphenylcarbamic chlorideHCID 19004143HCID 19004143, compound

Product 1

HCID 19004150HCID 19004150, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 364 mg (0.59 mmol) of (±) 2-(2-trityloxyethyl)-4-N-tritylpiperazine in 10 ml of N,N-dimethylformamide was added 170 ml (1.22 mmol) of triethylamine in one portion and 140 mg (0.60 mmol) of diphenylcarbamyl chloride in portions and the mixture was allowed to stir under nitrogen at room temperature for 20 hours. The solution was cooled and concentrated in vacuo. Flash chromatography on 40 g of silica gel using 25:75 v/v ethyl acetate/hexane as the eluant afforded 240 mg (50%) of a yellow oil.

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a817f539a52b415cb93a6c551bba035a
Source dataset
uspto-grants-1994_09
Patent number
US05344830

Reaction notes

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