HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2423754Generated: October 30, 2026
Ammonia → 6-{2-{[4-(2-Dimethylamino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol
https://huagongshe.com/reaction/2423754
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | 4-(2-Dimethylamino-2-methylpropoxy)benzaldehyde | HCID 23087245 | — |
| Reactant | 6-(2-(Ethylamino)-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl pivalate | HCID 57934095 | — |
| Reactant | Pivalic acid 6-{2-{[4-(2-dimethylamino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester | HCID 66626509 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 6-{2-{[4-(2-Dimethylamino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol | HCID 66627662 | 72% |
Reaction Steps
Synthesized from pivalic acid 6-(2-ethylamino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester and 4-(2-dimethylamino-2-methylpropoxy)benzaldehyde according to an analogous synthetic method to Example 212, to a solution of the resulting pivalic acid 6-{2-{[4-(2-dimethylamino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (73 mg) in tetrahydrofuran (1.5 ml) was added lithium aluminum hydride (20 mg), and the solution was stirred for 1.5 hours at room temperature. Tetrahydrofuran and aqueous ammonia were sequentially added thereto followed by stirring. The solution was then filtered through celite pad, the resulting residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system) to provide the title compound (45 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07960412B2 |
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| Source dataset | uspto-grants-2011_06 |
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| ORD ID | ord-d90af0d0244c4027ada1a4103f68ec28 |
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| Source note | uspto-grants-2011_06 |
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