1,4-Dioxane hydrochloride → HCID 66742844, compound

HRID 658830Notes

Reaction equation

HRID 658830 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][NH:18]C(=O)OC(C)(C)C)[CH:12]=[CH:13][CH:14]=1.[ClH:26].O1CCOCC1>C(Cl)Cl>[ClH:26].[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][NH2:18])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66628635HCID 66628635, compound

Product 1

HCID 66742844HCID 66742844, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 3-(3-(6-methoxyhex-1-ynyl)phenyl)propylcarbamate was deprotected following the method used in Example 13 except that CH2Cl2 was used as a cosolvent in the reaction (HCl-dioxane solution: CH2Cl2 7:5). Purification by prep HPLC (Method 2P) gave 3-(3-(6-methoxyhex-1-ynyl)phenyl)propan-1-amine hydrochloride as an off white solid. Yield (0.050 g, 30%): 1H NMR (400 MHz, CDCl3) δ 8.37 (br s, 3H), 7.10-7.24 (m, 4H), 4.02 (t, J=6.4 Hz, 2H), 3.78 (s, 3H), 2.98 (t, J=7.6 Hz, 2H), 2.69 (t, J=7.6 Hz, 2H), 2.44 (t, J=7.6 Hz, 2H), 2.04-2.12 (m, 2H), 1.82-1.89 (m, 2H), 1.63-1.73 (m, 2H).

Workup

  1. customPurification by prep HPLC (Method 2P)

Sources & evidence

ORD record
ord-cfac7ad6955c420d878483f0fcc090f1
Source dataset
uspto-grants-2011_12
Patent number
US08076516B2

Reaction notes

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