Hydrochloric Acid → HCID 53825613, compound

HRID 583403Notes

Reaction equation

HRID 583403 reaction equation
CN.[CH2:3]([O:5][C:6](=[O:22])[CH:7]=[C:8]([NH:20][CH3:21])[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[CH3:4].C([BH3-])#N.[Na+].Cl>C(O)C.C(O)(=O)C>[CH2:3]([O:5][C:6](=[O:22])[CH2:7][CH:8]([NH:20][CH3:21])[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 5003444Sodium cyanoborohydride2×HCID 67564170HCID 67564170, compound

Product 1

HCID 53825613HCID 53825613, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

2 ml (17.6 mmol) of a 27.3% solution of methylamine in ethanol and 5.5 ml of acetic acid are added to 24.9 g (92.5 mmol) of 3-methylamino-4-(2-naphthyl)-but-2-enoic acid ethyl ester in 250 ml of ethanol and the mixture is cooled to 0° C. 6.4 g (87 mmol) of 85% sodium cyanoborohydride and a further 5.5 ml of acetic acid are added to the suspension. The reaction mixture is allowed to rise to room temperature, with stirring, over a period of 2 hours. A further 0.64 g (8.7 mmol) of sodium cyanoborohydride is added to the clear solution and stirring is continued at room temperature for a further 2 hours. 400 ml of 1N hydrochloric acid are then added and the reaction mixture is stirred for 1 hour and then the ethanol is evaporated off in a rotary evaporator. The aqueous phase is washed twice with ether and the ether phases are extracted with 1N hydrochloric acid. Ethyl acetate is added to the combined aqueous phases and the mixture is rendered basic with solid potassium carbonate; the organic phase is separated off and washed with brine. The title compound is obtained in the form of a slightly brown oil. IR: 1725 cm-1 ; 1H-NMR, 200 MHz, CDCl3, delta, (ppm): 7.86-7.32 (m, 7H), 4.12 (q, 2H), 3.26 (quint., 1H), 3.05-2.82 (ABxd, 2H), 2.53-2.44 (s, 3H), 1.25 (t, 3H).

Workup

  1. customto rise to room temperature
  2. stirringstirring
  3. waitis continued at room temperature for a further 2 hours
  4. stirringthe reaction mixture is stirred for 1 hour
  5. customthe ethanol is evaporated off in a rotary evaporator
  6. washThe aqueous phase is washed twice with ether
  7. extractionthe ether phases are extracted with 1N hydrochloric acid
  8. additionEthyl acetate is added to the combined aqueous phases
  9. customthe organic phase is separated off
  10. washwashed with brine

Sources & evidence

ORD record
ord-014c96b91f9448f297903d892995ad96
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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