Hydrochloric Acid → HCID 90414615, compound

HRID 57410Notes

Reaction equation

HRID 57410 reaction equation
Cl.C(OC(=O)[NH:8][C@H:9]([C:11]1[N:12]=[N:13][N:14]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:15]=1)[CH3:10])(C)(C)C>O1CCOCC1>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([N:14]2[CH:15]=[C:11]([C@@H:9]([NH2:8])[CH3:10])[N:12]=[N:13]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90451725(S)-tert-butyl(1-(1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)ethyl)carbamate

Product 1

HCID 90414615HCID 90414615, compoundYield 115%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of hydrogen chloride (4.0 M in 1,4-dioxane, 3.3 mL, 13.2 mmol, 10 equiv) was added to a solution of (S)-tert-butyl(1-(1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)ethyl)carbamate (425 mg, 1.32 mmol) in 1,4-dioxane (5 mL) at room temperature. The solution was stirred for 1 hour, by which time a white precipitate had formed. The reaction was concentrated in vacuo to give the hydrochloride salt of (S)-1-(1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)ethanamine (338 mg, white solid) in 99% yield. The material was used without purification. 1H NMR (400 MHz, CD3OD) δ 8.68 (s, 1H), 7.90 (d, J=9.0 Hz, 2H), 7.63 (d, J=9.0 Hz, 2H), 4.77 (q, J=6.9 Hz, 1H), 1.78 (d, J=6.9 Hz, 3H). MS m/z 223.1 (M+H)+; Rt-0.50 min.

Workup

  1. customhad formed
  2. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-f4c64bd8d6dd4208a448de4e71065e2d
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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