4-(3-Bromopropyl)morpholine → 7-(3-Morpholinopropoxy)naphthalene-2-sulfonic acid

HRID 528806Notes

Reaction equation

HRID 528806 reaction equation
[O-:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([O-:15])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[Na+].[Na+].Br[CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[O:25]1[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][CH2:19][O:1][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][C:8]([S:12]([OH:15])(=[O:13])=[O:14])=[CH:9]3)=[CH:4][CH:3]=2)[CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 130340484-(3-Bromopropyl)morpholineHCID 86718866Sodium 7-oxidonaphthalene-2-sulfonate

Product 1

HCID 867188677-(3-Morpholinopropoxy)naphthalene-2-sulfonic acidYield 69%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 26B, sodium 7-oxidonaphthalene-2-sulfonate (Pfaltz and Bauer, 200 mg, 0.75 mmol) and 4-(3-bromopropyl)morpholine (310 mg, 1.49 mmol) were converted to the title compound (180 mg, 69%). 1H NMR (DMSO-d6) δ 9.53 (br s, 1H), 8.06 (s, 1H), 7.82 (d, J=9.0 Hz, 1H), 7.77 (d, J=8.6 Hz, 1H), 7.73-7.68 (m, 1H), 7.55 (dd, J=8.4, 1.5 Hz, 1H), 7.40 (d, J=2.2 Hz, 1H), 4.20 (t, J=5.8 Hz, 2H), 4.00 (d, J=11.0 Hz, 2H), 3.65 (t, J=11.6 Hz, 2H), 3.51 (d, J=12.3 Hz, 2H), 3.37-3.32 (m, 2H), 3.17-3.07 (m, 2H), 2.23-2.16 (m, 2H); MS (ESI+) m/z 350.3 (M+H)+.

Sources & evidence

ORD record
ord-33b5432c76e54f7ba133c994957a1971
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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