Water → HCID 13749149, compound

HRID 1732054Notes

Reaction equation

HRID 1732054 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[CH2:11][CH2:12][CH2:13][CH:14](O)[C:3]=12.C1(C)C=CC(S([Cl:25])(=O)=O)=CC=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.O>N1C=CC=CC=1>[ClH:25].[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[CH2:11][CH2:12][CH2:13][CH:14]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[C:3]=12

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8083MorpholineHCID 13749189HCID 13749189, compound

Product 1

HCID 13749149HCID 13749149, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6,7,8,9-tetrahydro-10-methylpyrido[1,2-a]indol-9-ol (2.01 g, 10 mmol, described in Example 2, Step 1) in dry pyridine (150 mL) was added a solution of p-toluenesulfonyl chloride (7.6 g, 40 mmol) in the same solvent (50 mL) at 0° C. Maintaining this temperature, stirring was continued for 60 minutes, and an excess of morpholine was added. The reaction mixture was stirred at ambient temperature for 3 hours, poured into water, and extracted with methylene chloride. The combined extracts were evaporated, and the residue was chromatographed. Elution with methylene chloride/methanol 20:1 afforded the title base. The hydrochloride salt was crystallized from EtOh, m.p. 172°-174° C.

Workup

  1. temperatureMaintaining this temperature
  2. stirringThe reaction mixture was stirred at ambient temperature for 3 hours
  3. extractionextracted with methylene chloride
  4. customThe combined extracts were evaporated
  5. customthe residue was chromatographed
  6. washElution with methylene chloride/methanol 20:1

Sources & evidence

ORD record
ord-9b6530b8841e4c21882a95d1ab86bed7
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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