Hydrochloric Acid → HCID 20141157, compound

HRID 543441Notes

Reaction equation

HRID 543441 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[I:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[CH2:14][CH2:15][CH:16](C)N.[C:19]1([CH2:25][CH:26]=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>CO>[I:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[CH2:14][CH2:15][CH2:16][N:2]([CH2:1][CH2:14][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:6]=1)[CH2:26][CH2:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 998PhenylacetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 20141156HCID 20141156, compound

Product 1

HCID 20141157HCID 20141157, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
125 °C

Procedure

A sample of 3.7 g (59 mmole) of sodium cyanoborohydride was added to a solution of 6.0 g (19.7 mmole) of 2 iodo-5-methoxy-α-methylbenzenepropanamine and 14.2 ml (0.12 mole) of phenylacetaldehyde in 60 ml of MeOH. Methanolic hydrogen chloride was added dropwise. After 16 hr the mixture was made frankly acidic by addition of methanolic hydrogen chloride. The mixture was stirred for one hour. The MeOH was evaporated in vacuo and the residue partitioned between ether and NaOH solution. The ether was evaporated in vacuo. The residue was redissolved in ether and ethereal hydrogen chloride added. The ether was decanted from the precipitated gum and the gum washed twice with ether. The gum was partitioned between NaOH solution and ether. The ether was washed with brine, dried and the solvent evaporated in vacuo. The volatile by products were removed by heating the residue up to 125° C. at 0.005 mm Hg in a Kugelrohr. The pot residue contained 9.1 g 26% yield of the title compound as a pale yellow oil.

Workup

  1. customThe MeOH was evaporated in vacuo
  2. customthe residue partitioned between ether and NaOH solution
  3. customThe ether was evaporated in vacuo
  4. dissolutionThe residue was redissolved in ether
  5. additionethereal hydrogen chloride added
  6. customThe ether was decanted from the precipitated gum
  7. washthe gum washed twice with ether
  8. customThe gum was partitioned between NaOH solution and ether
  9. washThe ether was washed with brine
  10. customdried
  11. customthe solvent evaporated in vacuo
  12. customThe volatile by products were removed

Sources & evidence

ORD record
ord-ab3010966bbd45d8986f611932a51d4b
Source dataset
uspto-grants-1987_04
Patent number
US04661635

Reaction notes

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