Triethylamine → 4-(4-Iodophenyl)morpholine

HRID 1531318Notes

Reaction equation

HRID 1531318 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][O:12][CH2:13][CH2:14]Br.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 108934-IodoanilineHCID 21521Bis(2-bromoethyl) ether

Product 1

HCID 27953584-(4-Iodophenyl)morpholine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 2-N-boc-amino-5-(4-morpholinophenyl)-pent-4-ynoate: 4-Iodoaniline (6.2 g, 28.4 mmol) is taken in 50 mL of DMF in the presence of 8 mL of bromoethyl ether and 10 mL of Et3N and heated to 60° C. for 24 hr. The mixture is then diluted with EtOAc, and washed 3x with dil. NaHCO3, 1x with brine, dried over MgSO4, filtered and evaporated. The residue is then recrystallized from MeOH to give 4.21 g of 4-iodophenylmorpholine as a pale brown solid.

Workup

  1. washwashed 3x with dil. NaHCO3, 1x with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is then recrystallized from MeOH

Sources & evidence

ORD record
ord-55cfd07e5a8f49d8af6616f4918f00b1
Source dataset
uspto-grants-2001_03
Patent number
US06197770B1

Reaction notes

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