Dimethylamine → HCID 20374134, compound

HRID 1834124Notes

Reaction equation

HRID 1834124 reaction equation
[C:1]([C:5]1[C:10]([OH:11])=[C:9]([CH3:12])[C:8]([CH3:13])=[C:7]([CH2:14]N(C)C)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[P:18]([O-:57])([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].[NH2-].[Li+].CNC>CN(C)C=O.C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.C(O)(=O)C.C1C=CC=CC=1>[C:1]([C:5]1[C:10]([OH:11])=[C:9]([CH3:12])[C:8]([CH3:13])=[C:7]([CH:6]=1)[CH2:14][P:18](=[O:57])([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])([CH3:4])([CH3:3])[CH3:2]

Participants

10

Reactant 4

HCID 674DimethylamineHCID 24532Lithium amideHCID 21884963HCID 21884963, compoundHCID 221015906-tert-Butyl-4-[(dimethylamino)methyl]-2,3-dimethylphenol

Product 1

HCID 20374134HCID 20374134, compound

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To 37.6 grams of the compound of Example 1 and 94 grams of di-n-octadecyl phosphite dissolved in 100 ml of dry N,N-dimethylformamide at 55° to 60° was added 2.16 grams of lithium amide and the reaction temperature raised to 106° and kept at 105° to 107° for 11/4 hours, the evolved dimethylamine being swept out of the reaction mixture by a stream of nitrogen. The reaction mixture was dissolved in about one liter of a solvent mixture of toluene, chloroform and benzene containing 6 grams of acetic acid, filtered free of some insoluble by-product. The clear filtrate was washed successively with water, 6N aqueous hydrochloric acid, and water until the wash water was in the pH range of 5 to 6. The solvent solution of the product was dried over anhydrous sodium sulfate. After removing the drying agent by filtration, the clear filtrate was freed of solvent by distillation at reduced pressures yielding a solid residue which afforded the desired compound as white crystals at 91° to 93° after crystallization from isopropanol (Compound 2).

Workup

  1. temperaturethe reaction temperature raised to 106°
  2. customkept at 105° to 107° for 11
  3. custom4 hours
  4. filtrationfiltered free of some insoluble by-product
  5. washThe clear filtrate was washed successively with water, 6N aqueous hydrochloric acid, and water until the wash water
  6. dry with materialThe solvent solution of the product was dried over anhydrous sodium sulfate
  7. customAfter removing the drying agent
  8. filtrationby filtration
  9. distillationthe clear filtrate was freed of solvent by distillation at reduced pressures
  10. customyielding a solid residue which

Sources & evidence

ORD record
ord-9f909a7bc2f84250aa0d0a649a03b08e
Source dataset
uspto-grants-1978_01
Patent number
US04069200

Reaction notes

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