Dichloromethane → Trifluoroacetic acid

HRID 1261998Notes

Reaction equation

HRID 1261998 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:9]1)=O)(C)(C)C.C(Cl)Cl.[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26]>>[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[CH2:9]1.[C:25]([OH:27])([C:24]([F:29])([F:28])[F:23])=[O:26]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66711120HCID 66711120, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 21327197HCID 21327197, compound

Procedure

3-Morpholin-4-yl-piperidine-1-carboxylic acid tert-butyl ester (2.70 g, 9.99 mmol) was dissolved in Methylene chloride (50.0 mL, 7.80E2 mmol) and the reaction mixture was treated with Trifluoroacetic Acid (6.0 mL, 78 mmol). The reaction was allowed to stir overnight at room temperature. The solvent was then removed en vacuo to afford the -Piperidin-3-yl-morpholine as a TFA salt. (M+H)=171.06. The crude product contained TFA which was neutralized in the next step. Crude NMR showed evidence of product formation. 1H NMR (400 MHz, DMSO, d6) δ 8.99 (m, 1H), 3.68 (m, 2H), 3.48 (m, 2H), 3.28 (m, 5H), 3.10 (m, 2H), 2.81 (m, 2H), 1.97 (m, 2H), 1.66 (m, 2H).

Workup

  1. customThe solvent was then removed en vacuo

Sources & evidence

ORD record
ord-ef75ad23802547bb8433d68134b0a00d
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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