2-Chloro-N,N-dimethylethylamine → 4-{2-[4-(2-Dimethylamino-ethoxy)-phenyl]-4-hydroxymethyl-4-methyl-cyclohex-1-enyl}-phenol

HRID 351438Notes

Reaction equation

[CH3:1][C:2]1([CH2:22][OH:23])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:3]1.[H-].[Na+].Cl[CH2:27][CH2:28][N:29]([CH3:31])[CH3:30]>CN(C=O)C>[CH3:30][N:29]([CH3:31])[CH2:28][CH2:27][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:4]2[CH2:3][C:2]([CH2:22][OH:23])([CH3:1])[CH2:7][CH2:6][C:5]=2[C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (1-methyl-3,4-di(4-hydroxy-phenyl)-cyclohex-3-enyl)-methanol (30 mg, 1 eq.) in DMF (1 mL) was added NaH (10 mg, 1 eq.), and the reaction mixture was then stirred for 2 h at 25° C. To the reaction mixture was then added (2-chloro-ethyl)-dimethyl-amine (12 mg, 1 eq) and the mixture stirred for 16 hours. The reaction mixture was then partitioned between H2O/ethyl acetate (5 mL/5 mL). The organic layer was separated, dried over MgSO4, concentrated and purified HPLC (20%˜80% CH3CN/H2O with 0.1% TFA) to yield 4-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-4-hydroxymethyl-4-methyl-cyclohex-1-enyl}-phenol.

Workup

customThe reaction mixture was then partitioned between H2O/ethyl acetate (5 mL/5 mL)
customThe organic layer was separated
dry with materialdried over MgSO4
concentrationconcentrated
custompurified HPLC (20%˜80% CH3CN/H2O with 0.1% TFA)

Sources & evidence

ORD record: ord-e64f4da5fc664fca941e963dae296254
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183445B2

Reaction notes

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