3,4-Dichlorophenethylamine → [2-(3,4-Dichloro-phenyl)-ethyl]-(2,2-dimethyl-benzo[1,3]dioxol-5-ylmethyl)-amine

HRID 855337

Reaktionsgleichung

Reaktionsgleichung von HRID 855337
C1(C2C=CC(CNCCC3C=CC(F)=C(C(F)(F)F)C=3)=CC=2)CC1.[CH3:25][C:26]1([CH3:37])[O:30][C:29]2[CH:31]=[CH:32][C:33]([CH:35]=O)=[CH:34][C:28]=2[O:27]1.[Cl:38][C:39]1[CH:40]=[C:41]([CH2:46][CH2:47][NH2:48])[CH:42]=[CH:43][C:44]=1[Cl:45].[BH4-].[Na+]>>[Cl:38][C:39]1[CH:40]=[C:41]([CH2:46][CH2:47][NH:48][CH2:35][C:33]2[CH:32]=[CH:31][C:29]3[O:30][C:26]([CH3:37])([CH3:25])[O:27][C:28]=3[CH:34]=2)[CH:42]=[CH:43][C:44]=1[Cl:45]

Komponenten

5

Edukt 4

HCID 2179583,4-DichlorophenethylamineHCID 5960122,2-Dimethylbenzo[d][1,3]dioxole-5-carbaldehydeHCID 4311764Sodium borohydrideHCID 69342889(4-Cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine

Produkt 1

HCID 69346783[2-(3,4-Dichloro-phenyl)-ethyl]-(2,2-dimethyl-benzo[1,3]dioxol-5-ylmethyl)-amine

Versuchsvorschrift

The title compound was synthesized in analogy to (4-cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine (described in example S53) using 83 mg of 2,2-dimethyl-benzo[1,3]dioxole-5-carbaldehyde (0.47 mmol) (described in example S119), 89 mg of 2-(3,4-dichloro-phenyl)-ethylamine (0.47 mmol) and 26 mg of sodium borohydride (0.70 mmol). The isolated colorless liquid (133 mg, 81%) was used in the following step without further purification. 1H NMR (CDCl3, 300 MHz): δ 1.66 (s, 6H), 2.76 (m, 2H), 2.86 (m, 2H), 3.68 (s, 2H), 6.66 (s, 1H), 6.68 (d, J=7.4 Hz, 2H), 7.04 (dd, J=8.2 and 2.1 Hz, 1H), 7.29 (d, J=2.1 Hz, 1H), 7.34 (d, J=8.2 Hz, 1H).

Aufarbeitung

  1. customThe isolated colorless liquid (133 mg, 81%) was used in the following step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-4044c480d84646338661cfaef28671c2
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259183B2

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