Water → 4-[7-(1-Adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzoic acid morpholide

HRID 618502Notes

Reaction equation

HRID 618502 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]12([C:17]3[CH:26]=[C:25]4[C:20]([CH:21]=[CH:22][C:23]([C:27]5[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=5)=[CH:24]4)=[CH:19][C:18]=3[O:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH3:42])[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2.O>C1COCC1>[C:7]12([C:17]3[CH:26]=[C:25]4[C:20]([CH:21]=[CH:22][C:23]([C:27]5[CH:35]=[CH:34][C:30]([C:31]([N:1]6[CH2:6][CH2:5][O:4][CH2:3][CH2:2]6)=[O:32])=[CH:29][CH:28]=5)=[CH:24]4)=[CH:19][C:18]=3[O:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH3:42])[CH2:16][CH:11]3[CH2:10][CH:9]([CH2:15][CH:13]([CH2:12]3)[CH2:14]1)[CH2:8]2

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 1317213724-[7-(1-Adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzoic acid chloride

Product 1

HCID 1317213734-[7-(1-Adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzoic acid morpholide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.8 ml (20.6 mmol) of morpholine and 40 ml of THF were introduced into a round-bottomed flask. A solution of 3.5 g (6.9 mmol) of 4-[7-(1-adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzoic acid chloride in THF was added dropwise and the reaction mixture was stirred at room temperature for two hours. The reaction mixture was poured into water and extracted with ethyl acetate and the organic phase was separated by settling, dried over magnesium sulfate and evaporated. The solid obtained was triturated in hexane, filtered and dried. 2.8 g (74%) of the expected amide were collected, which amide had a melting point of 86°-7° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe solid obtained
  6. customwas triturated in hexane
  7. filtrationfiltered
  8. customdried
  9. custom2.8 g (74%) of the expected amide were collected

Sources & evidence

ORD record
ord-11345ceee90e481193b59c6855e6de70
Source dataset
uspto-grants-1999_09
Patent number
US05952382

Reaction notes

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