Acetic Acid → HCID 18981768, compound

HRID 1440687Notes

Reaction equation

HRID 1440687 reaction equation
C([BH3-])#N.[Na+].[NH2:5][CH2:6][CH2:7][CH2:8][P:9]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)(=[O:11])[OH:10].[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([Cl:28])[CH:27]=1)[CH:23]=O.C(O)(=O)C>CO>[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([Cl:28])[CH:27]=1)[CH2:23][NH:5][CH2:6][CH2:7][CH2:8][P:9]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)(=[O:10])[OH:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 357463,5-DichlorobenzaldehydeHCID 1300223-Aminopropyl-cyclohexylmethylphosphinic acidHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18981768HCID 18981768, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.0 g of sodium cyanoborohydride are added in portions to a solution of 6.27 g of 3-aminopropyl-(cyclohexylmethyl)-phosphinic acid and 5.0 g of 3,5-dichlorobenzaldehyde and 1.91 g of glacial acetic acid in 50 ml of anhydrous methanol and the mixture is stirred at room temperature for 4 days. The solvent is removed, the white residue is taken up in 2.0M hydrochloric acid and filtered. The filtrate is concentrated to dryness by evaporation and the white solid that remains behind is suspended in ethyl acetate, filtered off and crystallised from propanol, yielding 3-[(3,5-dichlorobenzyl)amino]-propyl-(cyclohexylmethyl)-phosphinic acid, m.p. 231°-233°.

Workup

  1. customThe solvent is removed
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated to dryness by evaporation
  4. filtrationfiltered off
  5. customcrystallised from propanol

Sources & evidence

ORD record
ord-9e159da1b9cf413ea880beb9b1354435
Source dataset
uspto-grants-1996_03
Patent number
US05500418

Reaction notes

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