Hydrochloric Acid → HCID 70944882, compound

HRID 535799Notes

Reaction equation

HRID 535799 reaction equation
[ClH:1].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[CH2:18][C@H:17]2[NH:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1>[ClH:1].[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C@@H:16]2[CH2:18][C@H:17]2[NH:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=[CH:14][CH:15]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 51034697HCID 51034697, compound

Product 1

HCID 70944882HCID 70944882, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

HCl in 1,4 dioxane (4 mL) at 0° C. was added to a cooled solution of (trans)-2-(4-(benzyloxy)phenyl)-N-(2-(4-methylpiperazin-1-yl)ethyl)cyclopropanamine (120 mg, 1 equiv) in dioxane (5 mL) and stirred for 16 h. The progress of the reaction was monitored by TLC. After completion, it was filtered to obtain 62 mg of (trans)-2-(4-(benzyloxy)phenyl)-N-(2-(4-methylpiperazin-1-yl)ethyl)cyclopropanamine hydrochloride salt. Yield: 43%. 1H-NMR (DMSO-d6) δ (ppm): 1.21 (q, 1H), 1.54 (quin, 1H), 2.76 (s, 3H), 2.91 (br, 2H), 3.09 (br, 2H), 3.28 (br, 2H), 3.44 (br, 2H), 5.08 (s, 2H), 6.94 (d, 2H), 7.11 (d, 2H), 7.33 (m, 1H), 7.40 (m, 4H), 9.50 (br, 1H), 10.92 (br, 1H). MS (M+H): 366.2

Workup

  1. filtrationAfter completion, it was filtered

Sources & evidence

ORD record
ord-9780d5175e52465683d9cc2497770f59
Source dataset
uspto-grants-2014_10
Patent number
US08859555B2

Reaction notes

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