Formic Acid → HCID 15132166, compound

HRID 982309Notes

Reaction equation

HRID 982309 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[NH2:11][C:12]1[C:13]([Cl:30])=[CH:14][C:15]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][C@H:17]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:16]=2[CH:29]=1>C1COCC1>[CH:1]([NH:11][C:12]1[C:13]([Cl:30])=[CH:14][C:15]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][C@H:17]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:16]=2[CH:29]=1)=[O:3]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 11243154HCID 11243154, compound

Product 1

HCID 15132166HCID 15132166, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Formic acid (2.25 g, 95-97%) was added dropwise to acetic anhydride (4.10 g.) at 0° C. with stirring. The resulting solution was heated under nitrogen in a water bath at 50°-60° C. with stirring for 2 hours longer. The solution was cooled down to room temperature and diluted with 5 ml of THF. A solution of (R)-8-amino-7-chloro-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (5.10 g, 0.018 mol) in 25 ml of THF was added dropwise with stirring to the above solution. The resulting solution was stirred at room temperature for 3.5 hours longer and left standing at room temperature for 24 hours. The THF was evaporated in vacuo and the residue was treated with ether and 1N Na2CO3. The dried ether solution was evaporated in vacuo. The residue crystallized from acetonitrile, m.p. 135°-136° C. [α]26D +72.6° C. (DMF, c=1).

Workup

  1. temperatureThe resulting solution was heated under nitrogen in a water bath at 50°-60° C.
  2. stirringwith stirring for 2 hours longer
  3. stirringwith stirring to the above solution
  4. stirringThe resulting solution was stirred at room temperature for 3.5 hours longer
  5. waitleft
  6. customThe THF was evaporated in vacuo
  7. additionthe residue was treated with ether and 1N Na2CO3
  8. customThe dried ether solution was evaporated in vacuo
  9. customThe residue crystallized from acetonitrile, m.p. 135°-136° C. [α]26D +72.6° C. (DMF, c=1)

Sources & evidence

ORD record
ord-4f2be03d454540d387e849761f2a7b61
Source dataset
uspto-grants-1991_02
Patent number
US04996202

Reaction notes

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