Triethylamine → HCID 46897705, compound

HRID 1972099Notes

Reaction equation

HRID 1972099 reaction equation
[O:1]=[C:2](Cl)OC(Cl)(Cl)Cl.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([N:29]=[C:2]=[O:1])=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 154406Benzenamine, 4-(4-(4-methoxyphenyl)-1-piperazinyl)-

Product 1

HCID 46897705HCID 46897705, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a dichloromethane (400 mL) solution of diphosgene (74 mmol, 14.8 g) at 0° C. was added a dichloromethane (1100 mL) solution of 4-[4-(4-methoxyphenyl)-1-piperazinyl]benzenamine (Formula IIa, 41 mmol, 11.7 g) and triethylamine (93 mmol, 9.4 g) over a period of 3.5 hours. Once the addition was complete, the reaction was stirred in an ice bath for an additional 30 minutes. The reaction solvent was evaporated, the residue dissolved in tetrahydrofuran (300 mL), and the insolubles removed by filtration. The filtrate was concentrated by rotary evaporation to give 4-[4-(4-methoxyphenyl)-1-piperazinyl]-phenylisocyanate as a beige solid (12.8 g, 100% crude yield). The product was advanced to the next reaction step without purification. 1H NMR (400 MHz, CDCl3) δ 7.08-6.85 (m, -Ar), 3.79 (s, 3 H, OCH3), 3.45-3.20 (m, 8 H, CH2).

Workup

  1. additionOnce the addition
  2. customThe reaction solvent was evaporated
  3. dissolutionthe residue dissolved in tetrahydrofuran (300 mL)
  4. customthe insolubles removed by filtration
  5. concentrationThe filtrate was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-11b28816cfa243f6a6d4a33dc86c9abe
Source dataset
uspto-grants-2013_04
Patent number
US08431699B2

Reaction notes

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