Water → HCID 14850585, compound

HRID 260594Notes

Reaction equation

HRID 260594 reaction equation
[C:1]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:17]([CH3:22])([CH3:21])[CH2:16][CH2:15][C:14]([CH3:24])([CH3:23])[C:13]=3[CH:12]=2)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[C:27](OC(=O)C)(=[O:29])[CH3:28].C(N(CC)CC)C.O>ClCCl>[C:27]([N:10]([C:11]1[CH:20]=[CH:19][C:18]2[C:17]([CH3:21])([CH3:22])[CH2:16][CH2:15][C:14]([CH3:24])([CH3:23])[C:13]=2[CH:12]=1)[CH2:9][C:8]1[CH:25]=[CH:26][C:5]([C:1]([O:3][CH3:4])=[O:2])=[CH:6][CH:7]=1)(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 10315958HCID 10315958, compound

Product 1

HCID 14850585HCID 14850585, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.2 g (12 mmol) of N-(4-carbomethoxybenzyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine (from Example 11 ) and 1.6 ml (16 mmol) of acetic anhydride and 2.3 ml (17 mmol) of triethylamine in 100 ml of dichloromethane were stirred at room temperature. After the reaction was complete, the solution was poured into water and extracted with ethyl acetate, and the organic phase was separated off and evaporated; the residue was recrystallized from ethanol and yielded N-acetyl-N-(4-carbomethoxybenzyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine. 2.5 g of this product and 5.0 g of potassium hydroxide in 90 ml of 5:3:1 ethanol/water/dimethyl sulfoxide were then refluxed for 1 hour and, after cooling, three times the volume of ice-water was added and the pH was adjusted to 4 with 2N hydrochloric acid. The precipitate was filtered off and dried, yielding 1.5 g of the title compound of melting point 219°-223° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase was separated off
  3. customevaporated
  4. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-6c64736fcc074cda99561fc6adfe65d9
Source dataset
uspto-grants-1996_06
Patent number
US05527945

Reaction notes

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