Tetrahydrofuran → 4-[[Bis(p-dimethylaminophenyl)methoxy]acetyl]Morpholine

HRID 66929

Reaction equation

HRID 66929 reaction equation
[CH3:1][N:2]([C:4]1[CH:20]=[CH:19][C:7]([CH:8]([OH:18])[C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)[CH3:3].[CH3:21][O:22][CH3:23].[O:24]1CC[CH2:26][CH2:25]1.[CH3:29][N:30](C)[C:31](=N)N(C)C>CS(O)(=O)=O.CCCCCC>[CH3:17][N:15]([CH3:16])[C:12]1[CH:13]=[CH:14][C:9]([CH:8]([C:7]2[CH:19]=[CH:20][C:4]([N:2]([CH3:1])[CH3:3])=[CH:5][CH:6]=2)[O:18][CH2:26][C:25]([N:30]2[CH2:31][CH2:23][O:22][CH2:21][CH2:29]2)=[O:24])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8254Dimethyl EtherHCID 664601,1,3,3-TetramethylguanidineHCID 927424,4'-Bis(dimethylamino)benzhydrol

Product 1

HCID 204880364-[[Bis(p-dimethylaminophenyl)methoxy]acetyl]Morpholine

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 8058HexaneSolvent

Procedure

A solution of 4,4'-bis(N,N-dimethylamino)benzhydrol, methyl ether (9.0 g, 0.032 mole), glycol morpholinamide (4.6 g, 0.032 mole), 150 ml of tetrahydrofuran, 250 ml of n-hexane and 4 drops of methanesulfonic acid was refluxed for about 8 hours, during which time an additional 200 ml of solvent was added. The volume was reduced to 200 ml and the color was discharged with tetramethylguanidine. The solution was filtered hot and then cooled to precipitate a white solid. The solid was recrystallized from 350 ml of methyl cyclohexane to give 4.9 g of blue crystals; mp 147.8°-150° C.

Workup

  1. additionwas added
  2. filtrationThe solution was filtered hot
  3. temperaturecooled
  4. customto precipitate a white solid
  5. customThe solid was recrystallized from 350 ml of methyl cyclohexane

Sources & evidence

ORD record
ord-aedb3f7bf82141bca0c692617ca9a875
Source dataset
uspto-grants-1982_08
Patent number
US04343939

Linked notes

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