Acetic Acid → HCID 131722451, compound

HRID 1532395Notes

Reaction equation

HRID 1532395 reaction equation
C([BH3-])#N.[Na+].[C:5]1([CH2:11][CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][C:13]2=[O:22])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH2:23][CH2:24][CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1.[C:35]([OH:38])(=[O:37])[CH3:36].[C:39](=[O:42])([O-])[O-:40].[Na+].[Na+]>CO>[C:13]([OH:22])(=[O:40])/[CH:14]=[CH:36]/[C:35]([OH:38])=[O:37].[C:5]1([CH2:11][C@@H:12]2[C:21]3[C:16](=[CH:17][C:18]([O:42][CH3:39])=[CH:19][CH:20]=3)[CH2:15][CH2:14][C@@H:13]2[NH:23][CH2:24][CH2:25][C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[NH:28][CH:27]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:5]1([CH2:11][C@@H:12]2[C:21]3[C:16](=[CH:17][C:18]([O:37][CH3:35])=[CH:19][CH:20]=3)[CH2:15][CH2:14][C@@H:13]2[NH:23][CH2:24][CH2:25][C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[NH:28][CH:27]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 1150TryptamineHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 112648601-benzyl-2-tetralone

Product 1

HCID 131722451HCID 131722451, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (1.59 g, 25.3 mmol) was added to a solution of naphthalenone 7 (3.00 g, 12.7 mmol), tryptamine (2.03 g, 12.7 mmol), and acetic acid (0.76 g, 12.7 mmol) in methanol (100 mL). The reaction mixture was stirred for 20 h under nitrogen and then concentrated in vacuo to provide an orange-yellow solid. Saturated aqueous sodium carbonate solution was added to this residue, and the resulting mixture was extracted with chloroform. The chloroform extracts were combined, dried (Na2SO4), and concentrated to provide an orange-brown foam which was purified on flash silica gel (10% hexanes-chloroform to 1% methanol-chloroform) to provide the desired product as a red-beige foam. This material was dissolved in a minimum amount of acetone, and fumaric acid (0.84 g) was added. Diethyl ether and hexanes were added to precipitate a cream-colored solid and this material was crystallized from methanol to give 1.75 g (31%) of rac-cis-1-(phenylmethyl)-6-methoxy-N-(2-(3-indolyl)ethyl)-1,2,3,4-tetrahydro-2-naphthalenamine hemifumarate 8 (FIG. 4). mp 241.5-244.5° C. MS (PB-CH4), m/z 381 (MH+). 1H NMR (DMSO-d6) 1.80-2.00 (m, 2H), 2.40-2.50 (m 1H), 2.78-2.90 (m, 1H), 2.88-3.24 (m, 9H), 6.27 (d, J=7.7 Hz, 1H), 6.54 (s, 1H), 6.80 (br t, J=7.1 Hz, 1H), 6.88-7.28 (m, 11H), 7.35 (d, J=6.9 Hz, 1H), 7.57 (d, J=7.7 Hz, 1 H), 10.88 (br s, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customto provide an orange-yellow solid
  3. extractionthe resulting mixture was extracted with chloroform
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto provide an orange-brown foam which
  7. customwas purified on flash silica gel (10% hexanes-chloroform to 1% methanol-chloroform)

Sources & evidence

ORD record
ord-85fddfe1b2794a10b7c2f8efda75d2d2
Source dataset
uspto-grants-2001_03
Patent number
US06201025B1

Reaction notes

Loading…