Formaldehyde → HCID 59429652, compound

HRID 505159Notes

Reaction equation

HRID 505159 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([C:18]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]3[CH2:27][CH2:28][NH:29][CH2:30][C:19]=23)=[O:17])[CH2:12][CH2:11]1.[CH2:31](N(CC)CC)C.C=O.C([BH3-])#N.[Na+]>CO>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([C:18]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]3[CH2:27][CH2:28][N:29]([CH3:31])[CH2:30][C:19]=23)=[O:17])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 66743468HCID 66743468, compound

Product 1

HCID 59429652HCID 59429652, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.040 g (0.094 mmol) [4-(2-methoxy-phenyl)-piperidin-1-yl]-(1,2,3,4-tetrahydro-pyrazino[1,2-a]indol-10-yl)-methanone hydrochloride, 0.026 ml (0.19 mmol) triethylamine and 0.023 g (0.77 mmol) paraformaldehyde in 2 ml methanol was heated at reflux for 1 h. The reaction mixture was cooled to 0° C. on an ice-water bath and treated with 0.0089 g (0.14 mmol) sodium cyanoborohydride. After completed addition the mixture was allowed to warm to room temperature and stirred for 2 h. Quenching with water and dilution with 2 M aqueous sodium carbonate solution was followed by extraction with dichloromethane (2×50 ml). The combined organic layers were dried over sodium sulfate, concentrated in vacuo and purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.031 g, 82%) as an off-white solid.

Workup

  1. temperatureat reflux for 1 h
  2. additionaddition the mixture
  3. temperatureto warm to room temperature
  4. customQuenching with water and dilution with 2 M aqueous sodium carbonate solution
  5. extractionwas followed by extraction with dichloromethane (2×50 ml)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate)

Sources & evidence

ORD record
ord-7786517c547043ef8066258571d97d31
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

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