Formaldehyde → HCID 9798698, compound

HRID 897160Notes

Reaction equation

HRID 897160 reaction equation
Cl.[CH3:2][N:3]1[C:11]2[CH:10]=[CH:9][C:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])=[CH:7][C:6]=2[C:5]2[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:4]1=2.C=O.[C:28]([BH3-])#N.[Na+]>C(#N)C.C(O)(=O)C.C(OCC)(=O)C>[CH3:28][N:23]1[CH2:22][CH2:21][C:5]2[C:6]3[CH:7]=[C:8]([S:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)(=[O:13])=[O:14])[CH:9]=[CH:10][C:11]=3[N:3]([CH3:2])[C:4]=2[CH2:25][CH2:24]1

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10292950HCID 10292950, compound

Product 1

HCID 9798698HCID 9798698, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-methyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (EXAMPLE 13, 341 mg, 1.00 mmol) in acetonitrile (5 mL) is treated with formaldehyde (37%, 0.400 mL, 5.00 mmol), sodium cyanoborohydride (101 mg, 1.60 mmol) and glacial acetic acid (1 drop). After 5 hr, the mixture is diluted with ethyl acetate and then washed with water and saline. The organic layer is dried, filtered, and concentrated. The concentrate is dissolved in methylene chloride/methanol and treated with methanolic hydrochloric acid. The solvent is then removed and the residual solid crystallized from hot ethyl acetate/methanol to give the title compound, mp=283-286°; IR (drift) 2523, 2477, 2453, 2428, 1479, 1311, 1304, 1283, 1150, 1094, 756, 730, 694, 644 and 623 cm−1; NMR (300 MHz, DMSO-d6) δ 11.00, 8.16, 7.85-7.95, 7.50-7.65, 3.70, 3.15-3.45 and 2.89; MS (FAB) m/z 355 (MH+), 354, 353, 58 and 44; HRMS (FAB) calculated for C20H23N2O2S=355.1480, found=355.1488.

Workup

  1. washwashed with water and saline
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe concentrate is dissolved in methylene chloride/methanol
  6. additiontreated with methanolic hydrochloric acid
  7. customThe solvent is then removed
  8. customthe residual solid crystallized from hot ethyl acetate/methanol

Sources & evidence

ORD record
ord-483629ad104140cbaabfd58be5136fb5
Source dataset
uspto-grants-2005_07
Patent number
US06921823B2

Reaction notes

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