Hydrochloric Acid → (3-Cyclopropyl-4-fluorophenyl)methanamine hydrochloride

HRID 1093044Notes

Reaction equation

HRID 1093044 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:16]=[CH:17][C:18]=2[F:19])[CH2:7][NH:8]C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[ClH:27]>C(Cl)Cl.CCOCC>[ClH:27].[CH:1]1([C:4]2[CH:5]=[C:6]([CH2:7][NH2:8])[CH:16]=[CH:17][C:18]=2[F:19])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 57905173tert-Butyl 3-cyclopropyl-4-fluorobenzylcarbamate

Product 1

HCID 66588843(3-Cyclopropyl-4-fluorophenyl)methanamine hydrochlorideYield 92%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-cyclopropyl-4-fluorobenzylcarbamate (0.220 g, 0.829 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (5 mL, 64.9 mmol). The solution was stirred at room temperature for 1 h. To the solution was added 2M HCl in Et2O (5 mL). The solids were collected via filtration to give the title compound as a white solid (0.154 g, 92% yield). 1H NMR (400 MHz, MeOD) δ: 7.21-7.33 (1 H, m), 7.03-7.16 (2 H, m), 4.06 (2 H, s), 2.06-2.18 (1 H, m), 0.99-1.09 (2 H, m), 0.74-0.86 (2 H, m). 13C NMR (500 MHz, MeOD) δ: 162.09 (1C, d, J=245.84 Hz), 131.64 (1C, d, J=14.64 Hz), 128.98 (1C, d, J=3.08 Hz), 127.33 (1C, d, J=8.48 Hz), 126.78 (1C, d, J=4.62 Hz), 115.15 (1C, d, J=23.12 Hz), 42.43 (1C, s), 8.03 (1C, d, J=5.39 Hz), 7.04 (1C, s).

Workup

  1. filtrationThe solids were collected via filtration

Sources & evidence

ORD record
ord-9821f265369d4eae8013cb0afadebe3e
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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