Carbamate → 2-Morpholinoethylamine

HRID 852930Notes

Reaction equation

HRID 852930 reaction equation
COC1C=CC2N=C(N[C:11](=O)[NH:12][CH2:13][C:14]3C=CC(C(O)=O)=CC=3)SC=2C=1.[C:26](=[O:29])([O-])N.NC1S[C:33]2C=C(OC)C=C[C:34]=2[N:35]=1.NCC1C=CC(C(O)=O)=CC=1>>[NH2:35][CH2:34][CH2:33][N:12]1[CH2:11][CH2:26][O:29][CH2:14][CH2:13]1

Participants

5

Reactant 4

HCID 276CarbamateHCID 156302-Amino-6-methoxybenzothiazoleHCID 655264-(Aminomethyl)Benzoic AcidHCID 86601381HCID 86601381, compound

Product 1

HCID 4082852-MorpholinoethylamineYield 28%

Procedure

The title compound 165 was obtained following the same procedure as for the carbamate formation described in scheme 32, step 1 (example 75) substituting compound 129 for 2-amino-6-methoxybenzothiazole and using 4-aminomethylbenzoic acid instead of 4-(2-aminoethyl)-morpholine (28% yield). 1H NMR: (DMSO-d6) δ (ppm): 7.92 (t, J=8.0 Hz, 2H), 7.51 (d, J=8.5 Hz, 1H), 7.47 (s, 1H), 7.42 (d, J=8.5 Hz, 1H), 6.95 (d, J=7.0 Hz, 1H), 4.45 (s, 2H), 3.77 (s, 3H). m/z: 358.3 (MH+).

Sources & evidence

ORD record
ord-1027a9e3983742dd8b9299d7dae6e8fa
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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