Morpholine → HCID 70230899, compound

HRID 1976166Notes

Reaction equation

HRID 1976166 reaction equation
[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[CH:32]=[CH:31][C:24]([C:25]([O:27]CC=C)=[O:26])=[CH:23][CH:22]=5)=[CH:18]4)=[CH:13][C:12]=3[O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.N1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[CH:32]=[CH:31][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=5)=[CH:18]4)=[CH:13][C:12]=3[O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

5

Reactant 2

HCID 8083MorpholineHCID 70229209HCID 70229209, compound

Product 1

HCID 70230899HCID 70230899, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.5 g (2.58 mmol) of allyl 4-[7-(1-adamantyl)-6-ethoxycarbonylpentyloxy-2-naphthyl]benzoate, 50 ml of THF and 90 mg (0.08 mmol) of tetrakis(triphenylphosphine)palladium(0) were introduced into a three-necked flask under a stream of nitrogen. 1.13 ml (13 mmol) of morpholine were added dropwise and the reaction mixture was stirred at room temperature for two hours. The reaction mixture was evaporated to dryness, the residue was taken up in water, acidified to pH 1 with hydrochloric acid and extracted with ethyl ether and the organic phase was separated by settling, dried over magnesium sulfate and evaporated. The solid was triturated in heptane, filtered and dried. 1 g (72%) of the expected acid was collected, which acid had a melting point of 270°-1° C.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. extractionextracted with ethyl ether
  3. customthe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe solid was triturated in heptane
  7. filtrationfiltered
  8. customdried
  9. custom1 g (72%) of the expected acid was collected

Sources & evidence

ORD record
ord-a3296de871174f828b7f72dd348040cd
Source dataset
uspto-grants-2001_05
Patent number
US06225328B1

Reaction notes

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