Triethylamine → Methyl 2-[2-(morpholin-4-ylmethyl)-5-ethylphenoxy]propanoate

HRID 369449Notes

Reaction equation

[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][C:9]=2[OH:16])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+].Br[CH:31]([CH3:36])[C:32]([O:34][CH3:35])=[O:33]>C(#N)C>[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][C:9]=2[O:16][CH:31]([CH3:36])[C:32]([O:34][CH3:35])=[O:33])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 72.5 °C

Procedure

This compound was prepared in the manner of Example 4, using 221.0 grams (0.92 mole--1.0 equiv.) of 92.0% pure 2-(morpholin-4-ylmethyl)-5-ethylphenol, 202.3 grams (2.17 moles--2.36 equiv.) of triethylamine, 276.0 grams (2.17 moles--1.68 equiv.) of potassium carbonate, and 250.0 grams (1.63 moles--1.77 equiv.) of methyl 2-bromopropanoate in about 2000 mL (%Wt/Vol. Phenol to Solvent--11.1 %) of acetonitrile. This preparation differs in that the mixture was heated to 70° C. rather than 78° C. before the methyl 2-bromopropanoate was added and that the methyl 2-bromopropanoate was added during a 15 minute period at a rate to maintain the reaction temperature between 70-75° C. rather than during a ten minute period. A yield of 311 grams of 85.3% pure methyl 2-[2-(morpholin-4-ylmethyl)-5-ethylphenoxy]-propanoate was obtained (93.9% yield).

Workup

customThis compound was prepared in the manner of Example 4
additionwas added during a 15 minute period at a rate

Sources & evidence

ORD record: ord-c8e49bf566a14f249094c46c46e217c3
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136972

Reaction notes

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