Formaldehyde → HCID 22660570, compound

HRID 392768Notes

Reaction equation

HRID 392768 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][NH:16][CH:15]([CH3:19])[CH2:14]1)=[O:12])=[CH:5]2.[CH2:20]=O.[Na]>ClCCl.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH3:20])[CH:15]([CH3:19])[CH2:14]1)=[O:12])=[CH:5]2

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5360545SodiumHCID 22660603HCID 22660603, compound2×

Product 1

HCID 22660570HCID 22660570, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The product of Example 64, (5-Chloro-1H-indol-2-yl)-(3-methyl-piperazin-1-yl)-methanone (0.19 g) was dissolved in dichloromethane (10 mL). At room temperature, paraformaldehyde (0.031 g) was added, followed by acetic acid (1 drop). The reaction mixture was stirred at ambient temperature for 5 h. Sodium triacetoxybrohydride (0.318 g) was added. The reaction mixture was stirred at ambient temperature for 16 h and poured into dichloromethane (20 mL), washed with water, saturated sodium hydrogencarbonate solution and then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via silica gel chromatography (0-10% methanol/dichloromethane) to give the title compound (0.22 g). 1H NMR (400 MHz, CDCl3): δ 10.69 (br s, 1H), 7.56 (d, J=1.76 Hz, 1H), 7.33 (d, J=8.80 Hz, 1H), 7.16 (dd, J=1.96, 6.66 (d, J=1.57 Hz, 1H), 4.63-4.36 (m, 2H), 3.63-2.67 (m, 3H), 2.30 (s, 3H), 2.30-2.20 (m, 1H), 2.18-2.09 (m, 1H), 1.12 (d, J=5.87 Hz, 1H). MS (electrospray): exact mass calculated for C15H18ClN3O, 291.11; m/z found, 292.1 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 16 h
  2. washwashed with water, saturated sodium hydrogencarbonate solution
  3. dry with materialbrine, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via silica gel chromatography (0-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-dc2a62feaf41449ca66a29573c2066a5
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

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