Triethylamine → 4-Nitrophenyl morpholin-4-ylcarbamate

HRID 1366358Notes

Reaction equation

HRID 1366358 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[NH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(N(CC)CC)C>C(Cl)Cl>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2](=[O:3])[NH:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20315N-AminomorpholineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 207362844-Nitrophenyl morpholin-4-ylcarbamateYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-nitrophenyl chloroformate (27.8 g, 0.14 mole) in CH2Cl2 (350 mL) at 0° C. was added a solution of 4-aminomorpholine (10.2 g, 0.1 mole) and triethylamine (10.2 g, 0.1 mole) in CH2Cl2 (40 mL) via addition funnel over 1 h. A white ppt formed during the addition. After the addition was complete, the ice bath was removed and the reaction was stirred an additional 1 h. The solid was collected by filtration, re-suspended in Et2O and filtered to give the desired product as a white solid (15 g, 62% yield).

Workup

  1. additionvia addition funnel over 1 h
  2. customA white ppt formed during the addition
  3. additionAfter the addition
  4. customthe ice bath was removed
  5. filtrationThe solid was collected by filtration
  6. filtrationfiltered

Sources & evidence

ORD record
ord-0c7484699e224a3db16004493aaadc6c
Source dataset
uspto-grants-2011_02
Patent number
US07893057B2

Reaction notes

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