Hydrochloric Acid → HCID 67188291, compound

HRID 735867Notes

Reaction equation

HRID 735867 reaction equation
[CH2:1]([NH:13][C:14]([C:16]1[CH:30]=[CH:29][C:19]([CH2:20][NH:21]C(=O)OC(C)(C)C)=[CH:18][CH:17]=1)=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[ClH:31]>C(Cl)Cl>[ClH:31].[NH2:21][CH2:20][C:19]1[CH:18]=[CH:17][C:16]([C:14]([NH:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:15])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67187148HCID 67187148, compound

Product 1

HCID 67188291HCID 67188291, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[(dodecylamino)carbonyl]benzylcarbamate (2.35 g) in DCM (30 mL) was added a HCl solution (4N in dioxane, 30 mL). The resulting mixture was stirred at rt for 1 h. Evaporation of the solvents gave 4-(aminomethyl)-N-dodecylbenzamide hydrochloride compound as a white powder (1.97 g, 98%). M+(LC/MS(ESI)): 319.4; M−(LC/MS(ESI)): 317.4. HPLC (Condition A), Rt: 4.20 min (HPLC purity: 100%). 1H NMR (DMSO-d6, 300 MHz) δ 8.52 (br s, 3H), 7.87 (d, J=7.5 Hz, 2H), 7.56 (d, J=7.5 Hz, 2H), 4.06 (br s, 2H), 3.25-3.30 (m, 2H), 1.45-1.55 (m, 2H), 1.30-1.56 (m, 18H), 0.84 (t, J=8.3 Hz, 3H).

Workup

  1. customEvaporation of the solvents

Sources & evidence

ORD record
ord-48b30a4e43de48a59adfd8d5cb9e63b9
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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