Methoxyacetyl chloride → HCID 9838506, compound

HRID 2258574Notes

Reaction equation

HRID 2258574 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:13][CH2:14][NH2:15])=[CH:5][CH:4]=1.[CH3:16][O:17][CH2:18][C:19](Cl)=[O:20].[K+].[Br-]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:13][CH2:14][NH:15][C:19](=[O:20])[CH2:18][O:17][CH3:16])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 96623Methoxyacetyl chlorideHCID 253877Potassium BromideHCID 21996472HCID 21996472, compound

Product 1

HCID 9838506HCID 9838506, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-[2-(1,2,3,4-tetrahydro-7-methoxynaphthalen-1-yl)ethyl]amine was resolved according to the general procedure described in example 1 using L-tartartic add and was shown to have an enantiomeric excess of ≤99% by HPLC analysis. The HPLC analyses were carried out as described in example 3. The amine was converted to the amide according to General Procedure A using methoxyacetyl chloride. The final product was purified by reversed phase HPLC using acetonitrile/water to give a white solid. m.p.=58°-60° C.; 1H NMR (300 MHz, CDCl3) δ6.96 (d, J=8 Hz, 1H), 6.67 (s, 1H), 6.65 (m, 1H), 6.50 (bs, 1H), 3.86 (s, 2H), 3.76 (s, 3H), 3.43 (m, 2H), 3.38 (s, 3H), 2.79 (m, 1H), 2.66 (bm, 2H), 1.9-1.7 (bm, 4H), 1.67-1.63 (m, 2H); 3C NMR (75 MHz, CDCl3) δ169.44, 157.57, 141.26, 130.03, 129.24, 113.36, 111.82, 72.03, 59.17, 55.30, 36.94, 36.47, 35.66, 28.74, 27.52, 20.02; IR (KBr) 1658 cm-1 ; MS (DCI) m/e (MH)278; Analysis calc'd for C16H23N1O3 : C, 69.29; H, 8.36; N, 5.05; found: C, 69.17; H, 8.37; N, 4.92; [α] (20° C., 589 nm, CHCl3)=+6.96.

Workup

  1. additionadd
  2. customThe final product was purified by reversed phase
  3. customto give a white solid

Sources & evidence

ORD record
ord-f7f4216fb4cb4e16aa9c22a8a50c57ec
Source dataset
uspto-grants-1997_08
Patent number
US05661186

Reaction notes

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