Trifluoroacetic acid methylene chloride → (R)-N-ethyl-N-(morpholin-3-ylmethyl)ethanamine hydrochloride salt

HRID 1771214Notes

Reaction equation

HRID 1771214 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

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 66723762(R)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate2×

Product 1

HCID 66723935(R)-N-ethyl-N-(morpholin-3-ylmethyl)ethanamine hydrochloride saltYield 58%

Procedure

(R)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate (INTERMEDIATE 90, STEP 1) was dissolved with TFA/DCM, (6 ml, 1:1 v/v) and the resulting mixture was stirred for 1 h at room temperature. The volatiles were removed under reduced pressure and the concentrate was treated with 4N HCl in dioxane (3 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) and dried to give the title product (140 mg, yield: 58%).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionthe concentrate was treated with 4N HCl in dioxane (3 ml)
  3. stirringstirred for 10 minutes
  4. customthe volatiles were removed under reduced pressure
  5. customThe resulting semi solid was triturated with diethyl ether (2×30 ml)
  6. customdried

Sources & evidence

ORD record
ord-d883c166f7ba40a6bbb4eef3c076598f
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

Loading…