Methanesulfonic Acid → 1-(1-Methyl-1h-tetrazol-5-yl)-piperidin-4-amine methanesulphonic acid salt

HRID 602108Notes

Reaction equation

C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:18]([CH3:19])[N:17]=[N:16][N:15]=2)[CH2:10][CH2:9]1)(C)(C)C.[CH3:21][S:22]([OH:25])(=[O:24])=[O:23]>C(O)(C)C>[CH3:21][S:22]([OH:25])(=[O:24])=[O:23].[CH3:19][N:18]1[C:14]([N:11]2[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:13][CH2:12]2)=[N:15][N:16]=[N:17]1

Participants

Conditions

Temperature: 44 °C

Procedure

A mixture of tert-butyl[1-(1-methyl-1H-tetrazol-5-yl)-piperidin-4-yl]-carbamate (39.0 g, 0.138 mol) and methanesulphonic acid (23 mL, 0.354 mol) in isopropanol (290 mL) was stirred at 44° C. over night. The reaction mixture was cooled slowly to 0° C. and stirred for 2 hours. The precipitate was washed with cold isopropanol (2×25 mL) and dried to give 1-(1-methyl-1H-tetrazol-5-yl)-piperidin-4-amine methanesulphonic acid salt as a white powder (35.0 g). 1H NMR (300 MHz, MeOH-d4) ppm 1.75-1.94 (qd, J=12, 3 Hz, 2H) 2.03-2.19 (d, J=12 Hz, 2H) 2.71 (s, 3H), 3.08-3.26 (t, J=13 Hz, 2H) 3.37-3.50 (m, 1H) 3.63-3.87 (d, J=13 Hz, 2H) 3.94 (s, 3H) 4.74-4.90 (d, J=1 Hz, 3H).

Workup

temperatureThe reaction mixture was cooled slowly to 0° C.
stirringstirred for 2 hours
washThe precipitate was washed with cold isopropanol (2×25 mL)
customdried

Sources & evidence

ORD record: ord-3911d39d5b1c4e628e80d39aebd67d2c
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902373B2

Reaction notes

Loading…