Trifluoroacetic acid methylene chloride → (S)-N-ethyl-N-(morpholin-3-ylmethyl)ethanamine hydrochloride salt
Reaction equation
[CH2:1]([N:3]([CH2:6][C@H:7]1[CH2:12][O:11][CH2:10][CH2:9][N:8]1C(OC(C)(C)C)=O)[CH2:4][CH3:5])[CH3:2].C(O)(C(F)(F)F)=O.C(Cl)[Cl:28]>>[ClH:28].[CH2:1]([N:3]([CH2:6][C@H:7]1[CH2:12][O:11][CH2:10][CH2:9][NH:8]1)[CH2:4][CH3:5])[CH3:2]Participants
3
Procedure
(S)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate (INTERMEDIATE 86, STEP 1) was dissolved with TFA/DCM, (10 ml, 1:1 v/v) and the resulting mixture was stirred for 1 hour at room temperature. The volatiles were removed under reduced pressure and the concentrate was treated with 4N HCl in dioxane (5 ml), stirred for 10 minutes and the volatiles were removed under reduced pressure. The resulting semi solid was triturated with diethyl ether (2×30 ml), filtered and dried to give the title product (0.65 g, yield: 67%).
Workup
- customThe volatiles were removed under reduced pressure
- additionthe concentrate was treated with 4N HCl in dioxane (5 ml)
- stirringstirred for 10 minutes
- customthe volatiles were removed under reduced pressure
- customThe resulting semi solid was triturated with diethyl ether (2×30 ml)
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-7e6e43db23fb4e7294d5c52eac9d5f22
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09248140B2
Reaction notes
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