Benzenepropanal → HCID 178501215, compound

HRID 1757009Notes

Reaction equation

HRID 1757009 reaction equation
[ClH:1].[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.[C:13]1([CH2:19][CH2:20][CH:21]=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([BH3-])#N.[Na+]>CO.O>[ClH:1].[CH3:12][O:11][C:9]([C@H:6]1[CH2:5][CH2:4][C@H:3]([NH:2][CH2:21][CH2:20][CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:10]

Participants

6

Reactant 3

HCID 7707BenzenepropanalHCID 5003444Sodium cyanoborohydrideHCID 178501210HCID 178501210, compound

Product 1

HCID 178501215HCID 178501215, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2 g of methyl trans-4-aminocyclohexane-carboxylate-hydrochloride, 1.5 ml of 3-phenylpropionaldehyde and 1.3 g of sodium cyanoborohydride in 40 ml of dry methanol is stirred for 20 hours at ambient temperature. The mixture is diluted with water and extracted with ethyl acetate. The combined ethyl acetate phases are dried, acidified with ethereal hydrochloric acid and the solvent is removed under reduced pressure. The residue is triturated with acetone, suction filtered and washed with acetone and then with ether. Yield: 1.9 g (59.1% of theory), Melting point: 258°-260° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined ethyl acetate phases are dried
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is triturated with acetone, suction
  5. filtrationfiltered
  6. washwashed with acetone

Sources & evidence

ORD record
ord-53c51417b3664513a1ef0d1db3e67b2e
Source dataset
uspto-grants-1995_08
Patent number
US05442064

Reaction notes

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