Nitrogen mustard hydrochloride → N-(4-Morpholinophenyl)-8-(4-methylpiperazinyl)-5-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide

HRID 427341Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH:16]3[CH2:25][CH2:24][C:23]4[C:18](=[C:19]([NH2:28])[CH:20]=[CH:21][C:22]=4[O:26][CH3:27])[CH2:17]3)=[O:15])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl.Cl[CH2:31][CH2:32][N:33]([CH2:35][CH2:36]Cl)[CH3:34].C(=O)([O-])O.[Na+].[OH-].[NH4+]>C(O)CCC>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH:16]3[CH2:25][CH2:24][C:23]4[C:18](=[C:19]([N:28]5[CH2:36][CH2:35][N:33]([CH3:34])[CH2:32][CH2:31]5)[CH:20]=[CH:21][C:22]=4[O:26][CH3:27])[CH2:17]3)=[O:15])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of N-(4-morpholinophenyl)-8-amino-5-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide (1.4 g, 3.5 mmol), bis (2-chloroethyl)-methylamine hydrochloride (960 mg, 5 mmol) and sodium hydrogen carbonate (420 mg, 5 mmol) in n-butanol (30 mL) was heated at 90° C. for 5 h. After cooling, 2 M ammonium hydroxide (30 ml) was added and the mixture heated at 50° C. for 1 h. The phases were separated, evaporated in vacuo and purified by flash chromatography on a silica gel column with chloroform/ethanol/conc. ammonium hydroxide 90/10/0.3 as eluent. Yield: 320 mg (20%) of the title compound: mp 230-232° C.; EIMS (70 eV) m/z (relative intensity) 464 (75, M+).

Workup

temperatureAfter cooling
customThe phases were separated
customevaporated in vacuo
custompurified by flash chromatography on a silica gel column with chloroform/ethanol/conc

Sources & evidence

ORD record: ord-1fe6a1640375491880d6aebd0da287fb
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313118B1

Reaction notes

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