Chlorotrimethylsilane → HCID 23048846, compound

HRID 2106756Notes

Reaction equation

HRID 2106756 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:31])OC4C=CC=CC=4)=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:5][C:4]=1[CH3:32].Cl[Si](C)(C)C.Br.Br[CH2:40][CH2:41][NH2:42].[H-].[Na+].Br[CH2:46][CH2:47][CH3:48]>O.CN(C)C=O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[C:4]([CH3:32])=[CH:5][C:6]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH2:40][CH2:41][N:42]([CH2:46][CH2:47][CH3:48])[C:23]4=[O:31])=[CH:20][CH:21]=3)[CH2:12][CH2:11]2)=[CH:7][C:8]=1[CH3:9]

Participants

9

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 27742172-Bromoethylamine hydrobromideHCID 53641477HCID 53641477, compound

Product 1

HCID 23048846HCID 23048846, compoundYield 33.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of 17.2 parts of phenyl [4-[4-(4-methoxy-3,5-dimethylphenyl)-1-piperazinyl]phenyl]carbamate, 225 parts of N,N-dimethylformamide and 9.1 parts of N,N-diethylethanamine were added 9.6 parts of chlorotrimethylsilane. The whole was stirred first for 2 hours at room temperature and further for 2 hours at 80° C. After cooling, 10.1 parts of 2-bromoethanamine hydrobromide were added and stirring was continued for 1 hour. The resulting solution was added to a stirred mixture of 9.2 parts of a sodium hydride dispersion 50% and 45 parts of N,N-dimethylformamide. After stirring for 2 hours at room temperature, 6.15 parts of 1-bromopropane were added dropwise. Upon completion, stirring was continued overnight at room temperature. The reaction mixture was poured into water. The precipitated product was filtered off and crystallized from 2-propanol, yielding 5.6 parts (33.1%) of 1-[4-[4-(4-methoxy-3,5-dimethylphenyl)-1-piperazinyl]phenyl]- 3-propyl-2-imidazolidinone (int. 16).

Workup

  1. temperatureAfter cooling
  2. stirringstirring
  3. waitwas continued for 1 hour
  4. stirringAfter stirring for 2 hours at room temperature
  5. stirringUpon completion, stirring
  6. waitwas continued overnight at room temperature
  7. filtrationThe precipitated product was filtered off
  8. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-fdf83f59f7514d3fa3cad8c92914383f
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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