Hydrochloric Acid → HCID 178483345, compound

HRID 1744893Notes

Reaction equation

[CH3:1][N:2]([CH2:6][CH2:7][CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]#[N:5].[N:21]([Sn](CCCC)(CCCC)CCCC)=[N+:22]=[N-:23].[ClH:37]>C(OCC)C>[ClH:37].[CH3:1][N:2]([CH2:6][CH2:7][CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:3][C:4]1[NH:23][N:22]=[N:21][N:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 0.132 g (0.5 mmol) N-methyl-N-cyanomethyl-3,3-diphenylpropylamine (from step 2) and 0.183 g (0.55 mmol) azidotributyltin (Aldrich) was stirred at 80° C. under argon for 16 hours. The reaction mixture was suspended with 1 M solution of hydrogen chloride in diethyl ether (Aldrich) and the precipitated yellow wax was purified by preparative TLC with 10% methanol in ethyl acetate to give 0.06 g (yield 35%) N-methyl-N-[(1H-tetrazol-5-yl)methyl]-3,3-diphenylpropylamine hydrochloride (Compound A146) as a white powder. 1H NMR (DMSO-d6, 300 MHz) 7.30–7.16 (m, 10 H), 4.11 (s, 2 H), 3.97 (t, 1 H), 2.60 (br. s, 2 H), 2.45 (s, 3H), 2.36 (br. s, 2H).

Workup

customthe precipitated yellow wax was purified by preparative TLC with 10% methanol in ethyl acetate

Sources & evidence

ORD record: ord-5044c91bf8254c85b22f9f2870cd52ec
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07019024B2

Reaction notes

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