4-Bromophenol → 4-(2-(4-Bromophenoxy)ethyl)morpholine

HRID 545140Notes

Reaction equation

HRID 545140 reaction equation
Cl.Cl.[O:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15](C3C=CC(CC(NCC4C=CC=CC=4)=O)=NC=3)=[CH:14][CH:13]=2)[CH2:5][CH2:4]1.ClCCN1CCOCC1.[Br:44]C1C=CC(O)=CC=1>>[Br:44][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][N:6]2[CH2:7][CH2:8][O:3][CH2:4][CH2:5]2)=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 78084-BromophenolHCID 767274-(2-Chloroethyl)morpholine2×HCID 24989633N-Benzyl-2-(5-{4-[2-(morpholin-4-yl)ethoxy]phenyl}pyridin-2-yl)acetamide--hydrogen chloride (1/2)

Product 1

HCID 20538154-(2-(4-Bromophenoxy)ethyl)morpholine

Procedure

In another aspect, the invention relates to a process for preparing 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide dihydrochloride comprising the steps of: (1) reacting 4-(2-chloroethyl)morpholine with 4-bromophenol to yield 4-(2-(4-bromophenoxy)ethyl)morpholine; (2) coupling 4-(2-(4-bromophenoxy)ethyl)morpholine with 6-fluoropyridin-3-yl-3-boronic acid to yield 4-(2-(4-(6-fluoropyridin-3-yl)phenoxy)ethyl)morpholine; (3) reacting 4-(2-(4-(6-fluoropyridin-3-yl)phenoxy)ethyl)morpholine with acetonitrile to yield 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetonitrile; (4) converting 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetonitrile to methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate; (5) reacting methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate with benzylamine to yield 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide; and (6) contacting 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide with hydrochloric acid to yield 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide dihydrochloride.

Sources & evidence

ORD record
ord-abb8fc96c42349d0acaf394f477d1184
Source dataset
uspto-grants-2011_05
Patent number
US07935697B2

Reaction notes

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