Hydrochloric Acid → HCID 66714451, compound

HRID 1470553Notes

Reaction equation

HRID 1470553 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[CH:13][C:12]([C@@H:15]3[CH2:17][C@H:16]3[NH:18]C(=O)OC(C)(C)C)=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[ClH:28]>C(OCC)C>[ClH:28].[ClH:28].[F:27][C:2]([F:1])([F:26])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[CH:13][C:12]([C@@H:15]3[CH2:17][C@H:16]3[NH2:18])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86691194HCID 86691194, compound

Product 1

HCID 66714451HCID 66714451, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of tert-butyl (trans)-2-(6-(3-(trifluoromethyl)phenyl)pyridin-3-yl)cyclopropylcarbamate (70 mg, 0.185 mmol), in diethyl ether (10 mL) at 0° C. was added HCl in diethyl ether (5 mL) slowly dropwise over a period of 10 nuns, stirred the reaction mixture for 2 h. After completion, the reaction mixture was filtered under inert atmosphere and washed with hexane (10 mL) and EtOAC (5 mL), and dried under reduced pressure to get (50 mg, 86.2%) of (trans)-2-(6-(3-(trifluoromethyl)phenyl)pyridin-3-yl)cyclopropanamine dihydrochloride as a pale yellow powder. 1H-NMR (D2O) δ (ppm): 1.52 (q, 1H), 1.63 (quin, 1H), 2.66 (m, 1H), 3.08 (m, 1H), 7.72 (t, 1H), 7.89 (d, 1H), 7.98 (d, 1H), 8.09 (s, 1H), 8.14 (d, 1H), 8.27 (d, 1H), 8.61 (s, 1H). MS (M+H): 279.1.

Workup

  1. filtrationAfter completion, the reaction mixture was filtered under inert atmosphere
  2. washwashed with hexane (10 mL) and EtOAC (5 mL)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-141112e5b3b842b8a273cc310928a847
Source dataset
uspto-grants-2015_04
Patent number
US09006449B2

Reaction notes

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