Hydrochloric Acid → 6-benzyloxy-4-methoxymethyl-9{6-[N-methyl-N-(2-phenylethyl)-amino]-2-oxohexyl}9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester

HRID 1417962Notes

Reaction equation

HRID 1417962 reaction equation
[CH3:1][CH:2]([O:4][C:5]([C:7]1[N:27]=[CH:26][C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8]=1[CH2:28][O:29][CH3:30])=[CH:16][C:15]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:14][CH:13]=3)=[O:6])[CH3:3].[H-].[Na+].[CH3:33][N:34]([CH2:43][CH2:44][CH2:45][CH2:46][C:47](=[O:50])[CH2:48]Br)[CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.Cl>O1CCCC1.O>[CH3:3][CH:2]([O:4][C:5]([C:7]1[N:27]=[CH:26][C:10]2[N:11]([CH2:48][C:47](=[O:50])[CH2:46][CH2:45][CH2:44][CH2:43][N:34]([CH3:33])[CH2:35][CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:12]3[C:17]([C:9]=2[C:8]=1[CH2:28][O:29][CH3:30])=[CH:16][C:15]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:14][CH:13]=3)=[O:6])[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 65914AbecarnilHCID 867538606-[N-methyl-N-(2-phenylethyl)-amino]-2-oxohexylbromide

Product 1

HCID 867538596-benzyloxy-4-methoxymethyl-9{6-[N-methyl-N-(2-phenylethyl)-amino]-2-oxohexyl}9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-esterYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2.63 g of 6-benzyloxy-4-methoxymethyl-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methyl-ethyl)-ester (6.5 mmol) is taken up in 50 ml of dry tetrahydrofuran and mixed for deprotonation with 235 mg of 80% sodium hydride suspension in oil (7.1 mmol). It is allowed to stir for 20 more minutes at room temperature, then 2.22 g of 6-[N-methyl-N-(2-phenylethyl)-amino]-2-oxohexylbromide (7.1 mmol)--dissolved in 10 ml of tetrahydrofuran--is added. It is stirred for 12 hours at room temperature, mixed with 5 ml of 2N aqueous hydrochloric acid and diluted with water. It is then extracted with dichloromethane, the solvent is drawn off in a vacuum, and the crude product that is obtained is chromatographed on silica gel using hexane-ethyl acetate. 4.1 g of 6-benzyloxy-4-methoxymethyl-9{6-[N-methyl-N-(2-phenylethyl)-amino]-2-oxohexyl}9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester is obtained as a brownish oil.

Workup

  1. additionis added
  2. stirringIt is stirred for 12 hours at room temperature
  3. extractionIt is then extracted with dichloromethane
  4. customthe crude product that is obtained
  5. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-7482fdfcdb664e5ead19e2289724585d
Source dataset
uspto-grants-1999_03
Patent number
US05880126

Reaction notes

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