Sulfuric Acid → HCID 21930991, compound

HRID 1186900Notes

Reaction equation

C(OC([NH:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([NH2:19])=[O:18])[CH2:12]1)=O)(C)(C)C.S(=O)(=O)(O)O>CO.O1CCOCC1>[NH2:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([NH2:19])=[O:18])[CH2:12]1

Participants

Conditions

Temperature: 25 °C

Procedure

3-(2-tert-Butoxycarbonylaminoethyl)piperidine-1-carboxamide (392.7 mg, 1.45 mmoles) (prepared as described in Preparative Example 242, Step A above) was dissolved in methanol (7.5 mL) and 10% conc. sulfuric acid in 1,4-dioxane (19.5 mL) was added. The mixture was stirred at 25° C. for 1.25 h. The mixture was diluted with methanol and BioRad AG1-X8 resin (OH— form) was added until the pH was basic. The resin was filtered off, washed with methanol, evaporated to dryness and chromatographed on a silica gel column (30×2.5 cm) using 15% (10% conc, ammonium hydroxide in methanol)-dichloromethane as the eluant to give 3-(2-aminoethyl)piperidine-1-carboxamide (233 mg, 94%): FABMS: m/z 172.1 (MH+); HRFABMS: m/z 172.1444 (MH+). Calcd for C8H18N3O requires: m/z 172.1450; δH (CDCl3+3% CD3OD) 1.14 (1H, m, CH2), 1.40 (2H, m, CH2), 1.49 (1H, m, CH), 1.58 (1H, m, CH2), 1.69 (1H, m, CH2), 1.85 (1H, m, CH2), 2.55 (1H, m, CH2), 2.67 (5H, m, CH2/NH2), 2.76 (1H, bm, CH2), 2.84 (1H, m, CH2) and 3.82 ppm (2H, m, CONH2); δC (CDCl3+3% CD3OD) CH2: 24.8, 30.9, 36.6, 38.9, 44.9, 50.0; CH: 33.4.

Workup

additionresin (OH— form) was added until the pH
filtrationThe resin was filtered off
washwashed with methanol
customevaporated to dryness
customchromatographed on a silica gel column (30×2.5 cm)

Sources & evidence

ORD record: ord-2444377dcd0b4572aeefeebb80c4370d
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673924B2

Reaction notes

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