2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → HCID 66691633, compound

HRID 1808872Notes

Reaction equation

HRID 1808872 reaction equation
[NH2:1][C:2]1[C:3]([N+:22]([O-:24])=[O:23])=[CH:4][C:5]([Cl:21])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:7]=1.[CH3:25][N:26]([C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)[CH3:27].CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC>CN(C1C=CN=CC=1)C.ClCCCl.N1CCCCC1>[Cl:21][C:5]1[CH:4]=[C:3]([N+:22]([O-:24])=[O:23])[C:2]([NH:1][C:32](=[O:33])[C:31]2[CH:30]=[CH:29][C:28]([N:26]([CH3:25])[CH3:27])=[CH:36][CH:35]=2)=[CH:7][C:6]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:12][CH2:13]1

Participants

7

Reactant 3

HCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 44007824-(Dimethylamino)benzoyl chlorideHCID 22272887HCID 22272887, compound

Product 1

HCID 66691633HCID 66691633, compoundYield 70.9%

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of tert-butyl 4-(5-amino-2-chloro-4-nitrophenyl)piperazine-1-carboxylate (1.2 g, 3.36 mmol), 4-(N,N-dimethylamino)benzoyl chloride (803 mg, 4.37 mmol), BEMP (1846 mg, 6.73 mmol), and DMAP (411 mg, 3.36 mmol) in DCE (Volume: 15 ml) was heated at 85° C. foe 4 h. Cooled down and treated with a few drops of piperidine for 1 h. After the solvent was removed and mixture was diluted with MeOH, a orange precipitate formed. Filtration and washing with MeOH gave tert-butyl 4-(2-chloro-5-(4-(dimethylamino)benzamido)-4-nitrophenyl)piperazine-1-carboxylate (1.2 g, 2.381 mmol, 70.8% yield). 1H-NMR (CDCl3, 500 MHz): δ11.53 (1H, s), 8.82 (1H, s), 8.31 (1H, s), 7.89 (2H, d, J=8.85 Hz), 6.74 (1H, d, J=8.85 Hz), 3.64 (4H, m), 3.27 (4H, m), 3.09 (6H, s), 1.50 (9H, s).

Workup

  1. temperatureCooled down
  2. customAfter the solvent was removed
  3. additionmixture was diluted with MeOH
  4. customa orange precipitate formed
  5. filtrationFiltration
  6. washwashing with MeOH

Sources & evidence

ORD record
ord-aabbc8f259254fb69000d758247d5dd7
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

Loading…