Hydrochloric Acid → HCID 68673924, compound

HRID 333280Notes

Reaction equation

HRID 333280 reaction equation
[ClH:1].[CH3:2][NH:3][CH2:4][C:5]1([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[CH2:10][CH2:9][CH:8]=[CH:7][CH2:6]1>>[ClH:1].[CH3:2][NH:3][CH2:4][C:5]1([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[CH2:10][CH2:9][CH:8]=[CH:7][CH2:6]1

Participants

3

Reactant 2

HCID 313Hydrochloric Acid2×HCID 68673925HCID 68673925, compound

Product 1

HCID 68673924HCID 68673924, compound

Procedure

The title compound was formed as a byproduct in the reduction of the fluorinated carbamate. Preparative HPLC separation (chiralpak-AD column, 95:2.5:2.5:0.1 Hexanes:EtOH:MeOH:HNEt2) afforded the crude product, which was converted to the corresponding HCl salt by the addition of 2M HCl (Et2O) to the free amine. After stirring for 1 h, the white precipitate was filtered off to afford pure N-methyl-1-(1-(naphthalen-2-yl)cyclohex-3-enyl)methanamine hydrochloride salt (0.021 g). 1H-NMR (400 MHz, CDCl3) δ 9.04 (brs, 1H), 8.67 (brs, 1H), 7.79-7.67 (m, 4H), 7.45 (m, 3H), 5.80 (d, J=8.0 Hz, 1H), 5.59 (d, J=7.5 Hz, 1H), 3.21 (brs, 1H), 3.12 (brs, 1H), 2.89 (m, 1H), 2.57 (m, 1H), 2.22-1.99 (m, 2H), 2.15 (s, 6H), 1.75 (m, 2H). 13C-NMR (100 MHz, CDCl3) δ 138.6, 133.5, 132.6, 129.1, 128.6, 127.7, 127.2, 126.9, 126.6, 126.5, 124.3, 59.7, 40.0, 35.6, 33.7, 31.4, 22.5. LC-MS (m/z+) 252.1.

Workup

  1. customPreparative HPLC separation (chiralpak-AD column, 95:2.5:2.5:0.1 Hexanes:EtOH:MeOH:HNEt2)
  2. customafforded the crude product, which
  3. filtrationthe white precipitate was filtered off

Sources & evidence

ORD record
ord-8499ccc40c9a48558b996d837a2802fd
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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