Hydrochloric Acid → HCID 21071647, compound

HRID 1371978Notes

Reaction equation

HRID 1371978 reaction equation
[F:1][C:2]1[C:3]([F:14])=[C:4]2[C:11](=[CH:12][CH:13]=1)[C:7]([CH2:8][CH2:9][NH2:10])=[CH:6][NH:5]2.[N:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[CH:25]=O)=[CH:17][CH:16]=1.[BH4-].[Na+].Cl>CO.C(Cl)Cl.O>[F:1][C:2]1[C:3]([F:14])=[C:4]2[C:11]([C:7]([CH2:8][CH2:9][NH:10][CH2:25][C:24]3[CH:27]=[CH:28][CH:29]=[C:22]([O:21][C:18]4[CH:17]=[CH:16][N:15]=[CH:20][CH:19]=4)[CH:23]=3)=[CH:6][NH:5]2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 21071598HCID 21071598, compoundHCID 226082163-(4-Pyridinyloxy)benzaldehyde

Product 1

HCID 21071647HCID 21071647, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 21908982Water methylene chlorideSolvent

Procedure

Combine 6,7-difluoro tryptamine (0.285 g, 1.450 mmol), 3-pyridin-4-yloxybenzaldehyde (0.303 g, 1.52 mmol, 1.05 eq.) and molecular sieves 4 A (0.30 g) and stir in methanol (12 mL). After 4 h. filter the molecular sieves and wash several times with MeOH. To this MeOH solution, add portionwise NaBH4 (55.0 mg, 1.45 mmol), and stir at room temperature for 1 h. Remove MeOH in vacuo, dilute the residue with CH2Cl2/water, extract with CH2Cl2, combine organic layers, dry over Na2SO4 and concentrate in vacuo. Purification by flash chromatography on silica gel (CH2Cl2/MeOH) to give the free base which is converted to the hydrochloride salt: 1H NMR (300 MHz, DMSO-d6) 3.13 (s, 4H), 4.20 (s, 2H), 6.85–7.55 (m, 10H), 8.47–8.50 (m, 1H), 9.58 (br, 1H), 11.57 (br, 1H): MS (electrospray) m/e: 380.2 (M+1-HCl), 378.3 (M−1-HCl).

Workup

  1. filtrationAfter 4 h. filter the molecular sieves
  2. washwash several times with MeOH
  3. extractionextract with CH2Cl2
  4. dry with materialdry over Na2SO4
  5. concentrationconcentrate in vacuo
  6. customPurification by flash chromatography on silica gel (CH2Cl2/MeOH)
  7. customto give the free base which

Sources & evidence

ORD record
ord-9bf775d134714633bd6fc4a924a6f607
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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