HCID 86741386, compound → 2,2'-Azanediylbis[1-(3,4-dihydro-2H-1-benzopyran-2-yl)ethan-1-ol]

HRID 1906903Notes

Reaction equation

HRID 1906903 reaction equation
C1(C[N:8]([CH2:22][CH:23]([CH:25]2[CH2:30][CH2:29][C:28]3[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=3[O:26]2)[OH:24])[CH2:9][CH:10]([CH:12]2[CH2:17][CH2:16][C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[O:13]2)[OH:11])C=CC=CC=1.[H][H]>[Pd].CO>[NH:8]([CH2:9][CH:10]([CH:12]1[CH2:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[O:13]1)[OH:11])[CH2:22][CH:23]([CH:25]1[CH2:30][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[O:26]1)[OH:24]

Participants

5

Reactant 2

HCID 86741386HCID 86741386, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 1304802,2'-Azanediylbis[1-(3,4-dihydro-2H-1-benzopyran-2-yl)ethan-1-ol]

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3 parts of (A+A+)-α,α'-[[(phenylmethyl)imino]bis(methylene)]bis[3,4-dihydro-2H-1-benzopyran-2-methanol] and 120 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in dichloromethane. The organic phase was washed with a 10% sodium hydroxide solution and with water, dried, filtered and evaporated. The residue was dried in vacuo at 80° C., yielding 1.2 parts (19%) of (A+A+)-α,α'-[iminobis(methylene)]bis[3,4-dihydro-2H-1-benzopyran-2-methanol]; mp. 130.8° C.; [α]589 =+121.50° (c=1% CH3OH) (compound 74).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. washThe organic phase was washed with a 10% sodium hydroxide solution and with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was dried in vacuo at 80° C.

Sources & evidence

ORD record
ord-0ce1e55010a34bd58cf446c54ca70c71
Source dataset
uspto-grants-1987_03
Patent number
US04654362

Reaction notes

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