Dimethylamine → HCID 68966609, compound

HRID 2116407Notes

Reaction equation

Br[CH2:2][C@H:3]1[CH2:7][C:6]2[CH:8]=[C:9]([F:20])[CH:10]=[C:11]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:5]=2[O:4]1.[CH3:21][NH:22][CH3:23]>>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[C:11]1[C:5]2[O:4][C@@H:3]([CH2:2][N:22]([CH3:23])[CH3:21])[CH2:7][C:6]=2[CH:8]=[C:9]([F:20])[CH:10]=1

Participants

Reactant 2

HCID 674Dimethylamine

HCID 68963234HCID 68963234, compound

Product 1

HCID 68966609HCID 68966609, compoundYield 80%

Procedure

Treatment of (R)-2-bromomethyl-7-(2,6-dichloro-phenyl)-5-fluoro-2,3-dihydrobenzofuran (0.41 g, 1.1 mmol) and N,N-dimethylamine (2.0 M in tetrahydrofuran, 5.4 ml) generally according to the procedure described for Example 390 afforded 0.29 g (80%) of (R)-[7-(2,6-dichloro-phenyl)-5-fluoro-2,3-dihydro-benzofuran-2-ylmethyl]-dimethyl-amine as a white solid, hydrochloride salt. mp 156-158° C.; [α]D25=−21.04 (c 7.71 in methanol); Anal. calcd. for C17H16Cl2FNOHCl: C, 54.21; H, 4.55; N, 3.72. Found: C, 53.98; H, 4.62; N, 3.56.

Sources & evidence

ORD record: ord-8ba1b1ca3afc4aefbe726e2e94febd83
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435837B2

Reaction notes

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