Water → HCID 14850585, compound

HRID 1599122Notes

Reaction equation

HRID 1599122 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 21) 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-18e59122271f4457ace7a03c5a41bfda
Source dataset
uspto-grants-1998_04
Patent number
US05739374

Reaction notes

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